Butanoic acid, 4-chloro-4-oxo-, methyl ester → HCID 57983567, compound

HRID 1868918Notes

Reaction equation

HRID 1868918 reaction equation
Cl[C:2](=[O:9])[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[Br:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17]([CH3:22])([CH3:21])[C:16](=[O:23])[CH:15]=[C:14]2[OH:24]>ClCCCl.C(Cl)Cl>[C:2]([O:24][C:14]1[C:13]2[C:18](=[CH:19][CH:20]=[C:11]([Br:10])[CH:12]=2)[C:17]([CH3:22])([CH3:21])[C:16](=[O:23])[CH:15]=1)(=[O:9])[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 57983386HCID 57983386, compound

Product 1

HCID 57983567HCID 57983567, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 4-chloro-4-oxobutyrate (0.107 mL, 0.873 mmol) was added to a solution of 6-bromo-4-hydroxy-1,1-dimethylnaphthalen-2(1H)-one (0.212 g, 0.794 mmol), TEA (0.121 mL, 0.873 mmol) in 1,2-dichloroethane (3 mL). The mixture was diluted with DCM, washed with water, washed with NaHCO3, and dried over MgSO4. The crude product was purified by flash chromatography using EtOAc/hexane to afford 7-bromo-4,4-dimethyl-3-oxo-3,4-dihydronaphthalen-1-yl methyl succinate in 85% yield. 1H-NMR (300 MHz, CDCl3) δ ppm 7.74 (1H, d, J=2.0 Hz), 7.59 (1H, dd, J=8.4, 2.1 Hz), 7.36 (1H, d, J=8.5 Hz), 6.20 (1H, s), 3.73 (3H, s), 3.01 (2H, t, J=6.0 Hz), 2.80 (2H, t, J=6.0 Hz), 1.48 (6H, s). MS m/z: 381.

Workup

  1. washwashed with water
  2. washwashed with NaHCO3
  3. dry with materialdried over MgSO4
  4. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-65b6d363646147a89084085071e791f2
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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