Triethylamine → HCID 57978175, compound

HRID 1866518Notes

Reaction equation

HRID 1866518 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:8][C:9](=[O:20])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][OH:19])[CH:12]=1)[CH3:7].C(N(CC)CC)C>ClCCl>[CH2:6]([O:8][C:9](=[O:20])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][O:19][S:2]([CH3:1])(=[O:4])=[O:3])[CH:12]=1)[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57978286HCID 57978286, compound

Product 1

HCID 57978175HCID 57978175, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methane sulfonyl chloride (2.78 g, 24.3 mmol) was added dropwise to a solution of ethyl[3-(2-hydroxyethyl)phenyl]acetate (Preparation 55) (4.60 g, 22.1 mmol) and triethylamine (3.40 ml, 24.3 mmol) in dichloromethane (250 ml) at 0° C. under nitrogen. The reaction was allowed to warm to room temperature over 1 hour and washed with saturated aqueous sodium hydrogen carbonate (75 ml). The aqueous was washed with dichloromethane (2×100 ml) and the combined organics washed with water (25 ml), dried (sodium sulfate) and the solvent removed in vacuo to furnish the title compound as a colourless oil (6.2 g). 1H NMR (400 MHz, CDCl3): δ=7.29-7.25 (1H, t), 7.17-7.12 (3H, t), 4.41-4.38 (2H, t), 4.16-4.10 (2H, m), 3.58 (2H, s), 3.04-3.00 (2H, t), 2.81 (3H, s), 1.26-1.22 (3H, t) ppm. LRMS (electrospray): m/z [M+H]+ 578, [M−H]− 576.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate (75 ml)
  2. washThe aqueous was washed with dichloromethane (2×100 ml)
  3. washthe combined organics washed with water (25 ml)
  4. dry with materialdried (sodium sulfate)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-eeb8522c3f2b4078b61fe7a636b0412b
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

Loading…