Triethylamine → HCID 20448808, compound

HRID 358370

Reaction equation

HRID 358370 reaction equation
[Si:1]([O:8][C@@H: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].[SH:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21].C(N(CC)CC)C.[Cl-].[NH4+]>CO>[Si:1]([O:8][CH:9]1[CH2:10][C:11](=[O:15])[C:12]([S:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21])=[CH:13]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 5482614-Sulfanylbutan-1-olHCID 13362510HCID 13362510, compound

Product 1

HCID 20448808HCID 20448808, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.80 g (12.2 mmoles) of 4(R)-t-butyldimethylsilyloxy-2,3-epoxycyclopentanone and 1.30 g (12.2 mmoles) of 4-mercaptobutan-1-ol were dissolved in 12 ml of methanol, and with stirring 1.87 ml (13.5 mmoles) of triethylamine was added. The stirring was continued for 30 minutes. Ten milliliters of a saturated aqueous solution of ammonium chloride was added, and the mixture was concentrated. The residue was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated. The resulting oily product was chromatographed on a silica gel column using hexane/ethyl acetate (8/1) as an eluent to give 3.12 g (81%) of 4(RS)-t-butyldimethylsilyloxy-2-(4-hydroxybutylthio)-2-cyclopentenone.

Workup

  1. additionwas added
  2. concentrationthe mixture was concentrated
  3. extractionThe residue was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting oily product was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-50b7a521cf9c4e52b702724c63423584
Source dataset
uspto-grants-1984_08
Patent number
US04466980

Linked notes

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