Acetic Anhydride → HCID 57849365, compound

HRID 736523Notes

Reaction equation

HRID 736523 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:20]2[CH:33]=[CH:32][C:23]([O:24][CH2:25][C:26]([OH:31])([CH2:29][CH3:30])[CH2:27][CH3:28])=[C:22]([CH3:34])[CH:21]=2)([CH2:18][CH3:19])[CH2:16][CH3:17])=[CH:11][C:10]=1[CH3:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:43][C:44](OC(C)=O)=[O:45]>CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:20]2[CH:33]=[CH:32][C:23]([O:24][CH2:25][C:26]([O:31][C:44](=[O:45])[CH3:43])([CH2:27][CH3:28])[CH2:29][CH3:30])=[C:22]([CH3:34])[CH:21]=2)([CH2:16][CH3:17])[CH2:18][CH3:19])=[CH:11][C:10]=1[CH3:35])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 57849359HCID 57849359, compound

Product 1

HCID 57849365HCID 57849365, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A reaction mixture containing 3-{4-[1-(4-benzyloxy-3-methyl-phenyl)-1-ethyl-propyl]-2-methyl-phenoxymethyl}-pentan-3-ol (3.92 g, 8.27 mmol), Et3N (11.5 mL, 82.7 mmol) and Ac2O (3.9 mL, 41.3 mmol), is stirred at rt for 3 h. It is diluted with EtOAc (100 mL), washed with 0.1 M HCl (2×60 mL) and brine (60 mL); MgSO4 dried and concentrated to give the title compound (2.82 g, 5.47 mmol, 66%).

Workup

  1. washwashed with 0.1 M HCl (2×60 mL) and brine (60 mL)
  2. dry with materialMgSO4 dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d9abe05f10bd419eacee77f5752e72fa
Source dataset
uspto-grants-2009_09
Patent number
US07595345B2

Reaction notes

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