Chlorotrimethylsilane → (S)-4-trimethylsilyloxy-3-methyl-2-(2-propynyl)-cyclopent-2-ene-1-one

HRID 1079003Notes

Reaction equation

HRID 1079003 reaction equation
[OH:1][C@H:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][C:9]#[CH:10])=[C:3]1[CH3:11].C(N(CC)CC)C.Cl[Si:20]([CH3:23])([CH3:22])[CH3:21]>O1CCCC1>[CH3:21][Si:20]([CH3:23])([CH3:22])[O:1][C@H:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][C:9]#[CH:10])=[C:3]1[CH3:11]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 1569974-Hydroxy-3-methyl-2-(prop-2-yn-1-yl)cyclopent-2-en-1-one

Product 1

HCID 54351362(S)-4-trimethylsilyloxy-3-methyl-2-(2-propynyl)-cyclopent-2-ene-1-oneYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 To a solution of (S)-4-hydroxy-3-methyl-2(2-propynyl)-cyclopent-2-ene-1-one (12.88 g) and triethylamine (13.2 g) in tetrahydrofuran (200ml) was added dropwise chlorotrimethylsilane (10.4 g) for 5 minutes under ice-water cooling, then the solution was stirred for 2 hours under ice-water cooling, and 13 hours at room temperature. Then this solution was poured into ice-water and extracted twice with diethyl ether. The ether layers were combined and washed twice with brine. The separated organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resultant residue was subjected to column chromatography over florisil (eluent; n-hexane:ethyl acetate=20:1) to afford (S)-4-trimethylsilyloxy-3-methyl-2-(2-propynyl )-cyclopent-2-ene-1-one (18.0 g, yield 79.1% ) as a pale yellow oil.

Workup

  1. custom13 hours
  2. customat room temperature
  3. extractionextracted twice with diethyl ether
  4. washwashed twice with brine
  5. dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6e47574022244ce6bd0f8b235f00d13c
Source dataset
uspto-grants-1996_08
Patent number
US05550260

Reaction notes

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