Water → HCID 57276695, compound

HRID 1873094Notes

Reaction equation

HRID 1873094 reaction equation
[CH3:1][C:2]1[CH2:3][C@H:4]([OH:11])[CH2:5][C:6]([CH3:10])([CH3:9])[C:7]=1[CH3:8].N1C=CC=CC=1.FC(F)(F)S(O[Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])(=O)=O.O>C(Cl)Cl>[Si:24]([O:11][C@@H:4]1[CH2:5][C:6]([CH3:10])([CH3:9])[C:7]([CH3:8])=[C:2]([CH3:1])[CH2:3]1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 57184026HCID 57184026, compound

Product 1

HCID 57276695HCID 57276695, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

0.8 g (5.2 mmol) of the (1S)-3,4,5,5-tetramethyl-3-cyclohexen-1-ol obtained in Example 2B was dissolved in 5 ml of absolute methylene chloride, 0.5 ml of pyridine was added to the solution, and the mixture was cooled to 0° C. Subsequently 1.54 g (5.7 mmol) of tert-butyldimethylsilyl trifluorome-thanesulfonate were added and the mixture was stirred at 0° C. for 15 min and then poured into 10 ml of water. After extraction with 10 ml of methylene chloride, the organic phase was washed with 10 ml of 0.1 M H2SO4, 10 ml of saturated NaHCO3 solution and 10 ml of water, dried over MgSO4 and concentrated to result in 1.3 g (92% of theory) of the abovementioned product.

Workup

  1. extractionAfter extraction with 10 ml of methylene chloride
  2. washthe organic phase was washed with 10 ml of 0.1 M H2SO4, 10 ml of saturated NaHCO3 solution and 10 ml of water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto result in 1.3 g (92% of theory) of the abovementioned product

Sources & evidence

ORD record
ord-ec4af20c1bc74e80beea50d75963fbcf
Source dataset
uspto-grants-2000_08
Patent number
US06111125

Reaction notes

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