Ethyl bromoacetate → HCID 131713991, compound

HRID 1153895Notes

Reaction equation

HRID 1153895 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:8][O:9][C:10]1[CH:15]=[C:14]([CH2:16][NH:17][CH2:18][CH2:19][CH2:20][NH:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:27][CH2:28][CH2:29][NH2:30])[CH:13]=[CH:12][C:11]=1[OH:31].[CH2:32]([O:39][CH:40]1[C:45](=[O:46])[C:44]2[CH:47]=[CH:48][C:49]([C:51]([CH3:59])([CH3:58])[CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])=[CH:50][C:43]=2[O:42][C:41]1([CH3:61])[CH3:60])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[OH-].[NH4+]>COCOC.[Zn]>[CH3:8][O:9][C:10]1[CH:15]=[C:14]([CH2:16][NH:17][CH2:18][CH2:19][CH2:20][NH:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:27][CH2:28][CH2:29][NH2:30])[CH:13]=[CH:12][C:11]=1[OH:31].[CH2:32]([O:39][CH:40]1[C:45]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])([OH:46])[C:44]2[CH:47]=[CH:48][C:49]([C:51]([CH3:59])([CH3:58])[CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])=[CH:50][C:43]=2[O:42][C:41]1([CH3:60])[CH3:61])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 14923Ammonium HydroxideHCID 131713993HCID 131713993, compound

Product 1

HCID 131713991HCID 131713991, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8020DimethoxymethaneSolvent2×

Procedure

Zinc metal (13 g, 0.2 mole) is covered with a small amount of dimethoxymethane. The mixture is heated at reflux and a solution of 16.7 g (0.1 mole) ethyl bromoacetate in 75 ml of dimethoxymethane is added over 20 minutes. After refluxing for 30 minutes, the mixture is cooled to 0°-5° C. and 40.85 g (0.10 mole) dl-5-benzyloxy-2,2-dimethyl-7-(1,1-dimethylheptyl)-3,4-dihydro-2H-benzopyran-4-one is added dropwise. The mixture is stirred at 0°-5° C. for one hour, allowed to warm to room temperature and stirred overnight. Ammonium hydroxide, 25 ml, is added, the mixture extracted with ethyl ether and isolated as described in Part A above, to afford the desired product.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux
  3. temperatureAfter refluxing for 30 minutes
  4. temperaturethe mixture is cooled to 0°-5° C.
  5. stirringstirred overnight
  6. extractionthe mixture extracted with ethyl ether
  7. customisolated

Sources & evidence

ORD record
ord-b7ad27c3bb4c49dab70eaf3983c791aa
Source dataset
uspto-grants-1984_12
Patent number
US04486428

Reaction notes

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