Triethylamine → HCID 23361371, compound

HRID 233319Notes

Reaction equation

HRID 233319 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=2)=[N:4][C:3]=1[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30])=[CH:21][CH:20]=1.C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>ClCCl>[CH3:38][S:39]([O:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][C:22]1[CH:21]=[CH:20][C:19]([O:18][CH2:17][C:3]2[N:4]=[C:5]([C:7]3[CH:16]=[CH:15][C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH:8]=3)[O:6][C:2]=2[CH3:1])=[CH:24][CH:23]=1)(=[O:41])=[O:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23361361HCID 23361361, compound

Product 1

HCID 23361371HCID 23361371, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-[4-[5-methyl-2-(2-naphthyl)-4-oxazolylmethoxy]phenyl]pentan-1-ol (1.1 g), triethylamine (0.333 g) and dichloromethane (40 ml) was added dropwise, under ice-cooling, methanesulfonyl chloride (0.345 g). The mixture was stirred for 2 hours at room temperature, which was washed with water and dried (MgSO4). The solvent was distilled off to leave 5-[4-[5-methyl-2-(2-naphthyl)-4-oxazolylmethoxy]phenyl]pentyl methanesulfonate (1.21 g, 92%). Recrystallization from dichloromethane-ether gave colorless prisms, m.p.132°-133° C.

Workup

  1. additionwas added dropwise, under ice-
  2. temperaturecooling
  3. washwhich was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-0e13fbc523a147079f1456db72341af9
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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