Methanol → HCID 20448815, compound

HRID 358375Notes

Reaction equation

HRID 358375 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

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 5342591-Pentanol, 5-mercapto-HCID 13362509HCID 13362509, compound

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.

Workup

  1. customthe solvent was evaporated
  2. customto give 2.1 g of a crude product
  3. customto dry column chromatography

Sources & evidence

ORD record
ord-7314d9bdce254358b3ff22a3cf58e4e3
Source dataset
uspto-grants-1984_08
Patent number
US04466980

Reaction notes

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