Ethyl bromoacetate → HCID 131713991, compound

HRID 1608417Notes

Reaction equation

HRID 1608417 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×

Conditions

Temperature
2.5 °C

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 is 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. temperatureto warm to room temperature
  5. stirringstirred overnight
  6. extractionthe mixture is extracted with ethyl ether
  7. customisolated

Sources & evidence

ORD record
ord-02a7fccfa3bb49f984f4a8d6b3b15538
Source dataset
uspto-grants-1989_09
Patent number
US04870084

Reaction notes

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