Triethylamine → 3-({[Tert-butyl(diphenyl)silyl]oxy}methyl)-5-chlorobenzyl methanesulfonate

HRID 628385Notes

Reaction equation

HRID 628385 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[Si:13]([O:30][CH2:31][C:32]1[CH:33]=[C:34]([CH2:39][OH:40])[CH:35]=[C:36]([Cl:38])[CH:37]=1)([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[CH3:8][S:9]([O:40][CH2:39][C:34]1[CH:35]=[C:36]([Cl:38])[CH:37]=[C:32]([CH2:31][O:30][Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:33]=1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 123144720[3-({[tert-Butyl(diphenyl)silyl]oxy}methyl)-5-chlorophenyl]methanol

Product 1

HCID 1235758393-({[Tert-butyl(diphenyl)silyl]oxy}methyl)-5-chlorobenzyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (7.8 mL, 56 mmol) and methanesulfonyl chloride (2.9 mL, 37 mmol) were added to a solution of [3-({[tert-butyl(diphenyl)silyl]oxy}methyl)-5-chlorophenyl]methanol (7.65 g, 18.6 mmol, from Step 2) in DCM (50 mL) at 0° C. The cooling bath was removed and after reaction mixture warmed to room temperature, the reaction mixture was diluted with DCM and washed with water. The aqueous layer was extracted with two further portions of DCM. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-40% EtOAc/hexanes. Yield: (6.8 g, 75%).

Workup

  1. customThe cooling bath was removed
  2. customafter reaction mixture
  3. washwashed with water
  4. extractionThe aqueous layer was extracted with two further portions of DCM
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe product was purified by flash chromatography
  10. washeluting with a gradient from 0-40% EtOAc/hexanes

Sources & evidence

ORD record
ord-a5269669f92c494eb4c83c6f2b3b2297
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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