N,N-Dimethylaniline → HCID 86746455, compound

HRID 1645894Notes

Reaction equation

HRID 1645894 reaction equation
[CH2:1]([O:8][CH2:9]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)[C:13]1[CH:18]=[CH:17]C=CC=1.[CH3:20][CH:21]([CH2:54][CH3:55])[C:22]([O:24][CH:25]1[CH:34]2[CH:29]([CH2:30][CH2:31][CH:32]([CH3:45])[CH:33]2[CH2:35][CH2:36][CH:37]2[CH2:42][CH:41]([OH:43])[CH2:40][C:39](=[O:44])[O:38]2)[CH2:28][CH:27]([O:46][Si](C(C)(C)C)(C)C)[CH2:26]1)=[O:23].[CH2:56](Cl)Cl>C(OCC)(=O)C>[CH3:20][CH:21]([CH2:54][CH3:55])[C:22]([O:24][CH:25]1[CH:34]2[CH:29]([CH2:30][CH2:31][CH:32]([CH3:45])[CH:33]2[CH2:35][CH2:36][CH:37]2[CH2:42][CH:41]([O:43][CH2:9][O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:40][C:39](=[O:44])[O:38]2)[CH2:28][CH:27]([O:46][C:18]([CH3:17])([CH3:13])[CH3:56])[CH2:26]1)=[O:23]

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 6344Dichloromethane2×HCID 10932493benzyloxymethyl bromideHCID 77368066HCID 77368066, compound

Product 1

HCID 86746455HCID 86746455, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 23.1 g (115 mmol, 2.42 eq) of benzyloxymethyl bromide in 40 ml of methylene chloride at 0° C. was added 15.6 ml (123 mmol, 2.60 eq) of N,N-dimethylaniline and a solution of 24.9 g (47.4 mmol, 1.0 eq) of intermediate 3A in 50 ml of methylene chloride. This mixture was brought immediately to ambient temperature and stirred for 18 hours. The reaction mixture was then diluted with 400 ml of ethyl acetate, washed sequentially with saturated aqueous copper sulfate (1×200 ml, 1×75 ml) and brine (1×150 ml), dried with magnesium sulfate and concentrated. The product was isolated by elution from silica gel with 10% ethyl acetate in hexanes, yielding 29.4 g (96.1%) of intermediate 3B as a clear, colorless, viscous oil.

Workup

  1. customwas brought immediately to ambient temperature
  2. washwashed sequentially with saturated aqueous copper sulfate (1×200 ml, 1×75 ml) and brine (1×150 ml)
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated
  5. customThe product was isolated by elution from silica gel with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-31970190d97e472296f5ab43e568847b
Source dataset
uspto-grants-1993_01
Patent number
US05177104

Reaction notes

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