Triethylamine → HCID 18787488, compound

HRID 1602433Notes

Reaction equation

HRID 1602433 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[C:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[CH3:31][S:32]([O:1][CH2:2][CH2:3][CH2:4][C:5]1[C:15]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:14][CH:13]=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:34])=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18787388HCID 18787388, compound

Product 1

HCID 18787488HCID 18787488, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 2-(3-hydroxypropyl)-3-benzyloxybenzoate (10.19 g, 32.5 mmol), and triethyl amine (4.05 g, 40 mmol) in methylene chloride (100 ml) was cooled in an ice bath as methane sulfonyl chloride (2.79 ml, 36 mmol) was slowly added. The ice bath was removed and the reaction allowed to warm to room temperature over a 1 hr period. The mixture was diluted with water, and the methylene chloride layer was separated. The methylene chloride layer was washed with water twice, 1N HCl twice, and then filtered through a pad of silica gel to give a clear solution. This solution was concentrated in vacuo to give a clear oil (12.4 g, 98%).

Workup

  1. additionwas slowly added
  2. customThe ice bath was removed
  3. additionThe mixture was diluted with water
  4. customthe methylene chloride layer was separated
  5. washThe methylene chloride layer was washed with water twice
  6. filtration1N HCl twice, and then filtered through a pad of silica gel
  7. customto give a clear solution
  8. concentrationThis solution was concentrated in vacuo

Sources & evidence

ORD record
ord-ecd98723fad44ccaa139f368101f06a0
Source dataset
uspto-grants-1999_11
Patent number
US05981571

Reaction notes

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