J. Org. Chem., Vol. 36, No. $4, i97i 3743
NUCLEOSIDES of 1.12 g of 7a in 25 ml of MeCN was added to the cell over a period of 60 rnin and reduction was continued for 100 min longer. VDC(10% silicone rubber on Chromosorb W, 200’) of the CHClasoluble product indicated the formation of ethyl fi-phenylpropionate (10) (ll’%),identified by comparison with an authentic sample. Acidification of the aqueous layer t o pH 1 and extraction vi.ith CHC1, gave 400 mg (43%) of phenylpropiolic acid.
Repetition of the procedure but with 2 equiv of anhydrous HBr added to the substrate solution raised the yield of 10 to 26%. With 4 equiv of HBr the yield of 10 was 55%.
Registry No.-2a, 31892-93-0; 2c, 6258-32-8; 2d, 31892-95-2; 3, 31892-96-3; Sa, 24393-65-5; 5b, 3189298-5; 6, 31892-99-6; 7a, 2216-94-6; 7b, 29577-38-6; 7 ~ 931893-02-4.
Nucleosides. XIV. Synthesis of 3’-Deoxyadenosine and 9-(3-Deoxy-a-~-threo-pentofuranosyl)adenine
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