Water → HCID 23047899, compound

HRID 2107138Notes

Reaction equation

HRID 2107138 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:6][CH:5]=1.[Br:26]N1C(=O)CCC1=O.O>O1CCCC1>[Br:26][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 67184N-bromobutanimideHCID 23047964HCID 23047964, compound

Product 1

HCID 23047899HCID 23047899, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8.1 g (0.186 mol) of 55% sodium hydride in a mineral oil suspension is added in portions to a solution of 63.4 g (0.186 mol) of ethyl 7-(4-chlorophenyl)-2-ethoxycarbonylheptanoate (BM 13.861) in 500 ml of absolute tetrahydrofuran, and stirred for another 15 minutes to complete the salt formation. Then 33.1 g (0.186 mol) of N-bromosuccinimide is added and the mixture is stirred for 8 h at room temperature. Then it is poured into water, acidified, and extracted with ether. The combined extracts are washed, dried and concentrated by evaporation. The concentrate is chromatograhied with toluene on silica gel. 61.3 g (78% of theory) of ethyl 2-bromo-7-(4-chlorophenyl)-2-ethoxycarbonylheptanoate, a colorless oil, is obtained.

Workup

  1. stirringthe mixture is stirred for 8 h at room temperature
  2. extractionextracted with ether
  3. washThe combined extracts are washed
  4. customdried
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-7fa7a00dcb5e4d33a0dbf6a1022bf726
Source dataset
uspto-grants-1990_06
Patent number
US04933367

Reaction notes

Loading…