Methanol → HCID 20448815, compound

Reaction equation

[Si:1]([O:8][CH:9]1[CH2:13][C:12](=O)[CH:11]2[O:15][CH:10]12)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][SH:22].C(N(CC)CC)C.[CH3:30][OH:31]>>[Si:1]([O:8][CH:9]1[CH2:10][C:11](=[O:15])[C:12]([S:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:30][OH:31])=[CH:13]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

Reactant 4

HCID 887Methanol

HCID 8471Triethylamine

HCID 5342595-Mercapto-1-pentanol

HCID 133625094(RS)-t-butyldimethylsilyloxy-2,3-epoxycyclopentanone

Product 1

HCID 20448815HCID 20448815, compoundYield 31%

Procedure

1.26 g (5.94 mmoles) of 4(RS)-t-butyldimethylsilyloxy-2,3-epoxy cyclopentanone and 804 mg (6.0 mmoles) of 5-hydroxy-1-pentanethiol were dissolved in 10 ml of methanol, and 606 mg (6 mmoles) of triethylamine was added. After the reaction was carried out for 10 minutes, the solvent was evaporated to give 2.1 g of a crude product. The crude product was subjected to dry column chromatography and developed with hexane/ethyl acetate (7/3) to give 710 mg (2.16 mmoles; yield 31%) of 4-t-butyldimethylsilyloxy-2-(6-hydroxyhexylthio)-2-cyclopentenone.