Water → Methanesulfonic acid 2-(4-chloro-benzyloxy)-ethyl ester

HRID 2261245Notes

Reaction equation

HRID 2261245 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:17]=[CH:16][C:10]([CH2:11][O:12][CH2:13][CH2:14][OH:15])=[CH:9][CH:8]=1.C(N(C(C)C)CC)(C)C.O>C(Cl)Cl>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][O:12][CH2:13][CH2:14][O:15][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 27637512-[(4-Chlorobenzyl)oxy]-1-ethanol

Product 1

HCID 59593471Methanesulfonic acid 2-(4-chloro-benzyloxy)-ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulfonyl chloride (980 μL, 12.6 mmol) in dry DCM (10 mL) was slowly added to a cooled (0° C.) solution of 2-(4-chloro-benzyloxy)-ethanol (2.14 g, 11.46 mmol) and diisopropyethylamine (2.0 mL, 23 mmol) in dry DCM (10 mL). The reaction mixture was allowed to warm to RT overnight. Water was added and the organic layer was dried (MgSO4) and concentrated. The residue was purified by column chromatography over silica using a gradient of 0-20% diethyl ether/cyclohexane to afford the pure product.

Workup

  1. dry with materialthe organic layer was dried (MgSO4)
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography over silica using a gradient of 0-20% diethyl ether/cyclohexane
  4. customto afford the pure product

Sources & evidence

ORD record
ord-58bc85cb922144c3bfaba53750531d1d
Source dataset
uspto-grants-2010_12
Patent number
US07846955B2

Reaction notes

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