Triethylamine → HCID 178455455, compound

HRID 2118237Notes

Reaction equation

HRID 2118237 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].CCN(CC)CC>C(Cl)Cl>[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) of trans-[4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexyl]-methanol and 9.99 mL (128 mmol, 1.2 eq) of methanesulfonyl chloride in 350 mL of CH2Cl2 were added under stirring at 0-10° C. 29.6 mL (213 mmol, 2 eq) of Et3N within 20 min. The reaction mixture was then stirred at RT for 1 h. It was then partitioned between CH2Cl2, 1M HCl and water. The CH2Cl2-phase was dried over MgSO4 and concentrated to yield 38.2 g of crude trans-methanesulfonic acid 4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexylmethyl ester as colorless viscous oil, MS: 354 (M+NH4+).

Workup

  1. additionwere added
  2. stirringThe reaction mixture was then stirred at RT for 1 h
  3. customIt was then partitioned between CH2Cl2, 1M HCl and water
  4. dry with materialThe CH2Cl2-phase was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c221c22bc1304c25a6ab1f0b13a03ed1
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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