1-(Trimethylsilyl)prop-1-yne → (1RS,4RS)-4-hydroxy-4-(3-trimethylsilyl-2-propynyl)-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether

HRID 582748Notes

Reaction equation

HRID 582748 reaction equation
[CH3:1][Si:2]([C:5]#[C:6][CH3:7])([CH3:4])[CH3:3].C([Li])CCC.[Si:13]([O:20][CH:21]1[CH2:25][C:24](=[O:26])[CH:23]=[CH:22]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>O1CCCC1.CCCCCC>[Si:13]([O:20][CH:21]1[CH2:25][C:24]([OH:26])([CH2:7][C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])[CH:23]=[CH:22]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 803631-(Trimethylsilyl)prop-1-yneHCID 41316994-((tert-Butyl(dimethyl)silyl)oxy)cyclopent-2-en-1-oneHCID 178418339Butyllithium

Product 1

HCID 86754280(1RS,4RS)-4-hydroxy-4-(3-trimethylsilyl-2-propynyl)-2-cyclopenten-1-yl (t-butyldimethylsilyl) etherYield 59%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution mixture of 6.5 g of trimethylsilyl-1-propyne and 50 ml of tetrahydrofuran was added under nitrogen stream and at -30° C. 17.4 ml of 1.56 M hexane solution of n-butyllithium and the resulting mixture was stirred at the same temperature for 1 hour. Then, a solution mixture of 10 g of (RS)-4-oxo-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether and 100 ml of tetrahydrofuran was added by drops to the reaction solution obtained above, and the resulting mixture was stirred for further one hour. The reaction liquid thus obtained was after-treated and purified in the same manner as in (2) of the intermediate preparation example 1 to obtain 8.9 g of (1RS,4RS)-4-hydroxy-4-(3-trimethylsilyl-2-propynyl)-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether. Yield 59%

Workup

  1. additionwas added under nitrogen stream
  2. customat -30° C
  3. additionwas added by drops to the reaction solution
  4. customobtained above, and the resulting mixture
  5. customThe reaction liquid
  6. customthus obtained
  7. additionwas after-treated
  8. custompurified in the same manner as in (2) of the intermediate preparation example 1

Sources & evidence

ORD record
ord-b770930a292847199550311c0dc32340
Source dataset
uspto-grants-1999_07
Patent number
US05925676

Reaction notes

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