Triethylamine → HCID 178455455, compound

HRID 967148Notes

Reaction equation

HRID 967148 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:17])([CH3:16])[C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:18][S:19](Cl)(=[O:21])=[O:20].C(N(CC)CC)C>ClCCl>[C:1]([SiH2:5][O:6][C:7]([CH3:17])([CH3:16])[C@H:8]1[CH2:9][CH2:10][C@H:11]([CH2:14][O:15][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:12][CH2:13]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178455454HCID 178455454, compound

Product 1

HCID 178455455HCID 178455455, compoundYield 106.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

To an ice-cooled solution of 27.6 g (107 mmol) trans-[4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexyl]-methanol and 9.99 ml (128 mmol) of methanesulfonyl chloride in 350 ml of dichloromethane was added under stirring at 0-10° C. 29.6 ml (213 mmol) triethylamine within 20 minutes. The reaction-mixture was then stirred for 1 hour at room temperature. It was then partitioned between dichloromethane, 1N HCl and water. The dichloromethane-phase was dried over magnesium sulfate and concentrated to yield 38.2 g crude trans-methanesulfonic acid 4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexylmethyl ester as colorless viscous oil, MS: 354 (M+NH4+).

Workup

  1. additionwas added
  2. stirringThe reaction-mixture was then stirred for 1 hour at room temperature
  3. customIt was then partitioned between dichloromethane, 1N HCl and water
  4. dry with materialThe dichloromethane-phase was dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8f18bdacc9b942fab17f205fa485e23c
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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