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Water → Methyl 4-{1-[2-tert-butoxy-1-(4-chlorophenyl)-2-oxoethyl]butyl}benzoate

HRID 2190889
Notes
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Reaction equation

HRID 2190889 reaction equation
CC([O-])(C)C.[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:10][CH:9]=1.Br[CH:23]([C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=1)[CH2:24][CH2:25][CH3:26].O>CN(C=O)C>[C:18]([O:17][C:15](=[O:16])[CH:14]([CH:23]([C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=1)[CH2:24][CH2:25][CH3:26])[C:11]1[CH:10]=[CH:9][C:8]([Cl:7])=[CH:13][CH:12]=1)([CH3:21])([CH3:20])[CH3:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 13380183(4-Chlorophenyl)acetic acid tert-butyl esterHCID 22399772Methyl 4-(1-bromobutyl)benzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 58349494Methyl 4-{1-[2-tert-butoxy-1-(4-chlorophenyl)-2-oxoethyl]butyl}benzoate

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Procedure

To a suspension of KOtBu (980 mg, 8.73 mmol) in anhydrous DMF (15 mL) at 0° C. was added tert-butyl 4-chlorophenylacetate (1.80 g, 7.94 mmol). After stirring for two minutes, a solution of methyl 4-(1-bromobutyl)benzoate in DMF (5 mL) was added dropwise. The mixture was allowed to warm to room temperature. After stirring for 20 minutes, water was added then the solution was extracted with CH2Cl2 (2×100 mL). The combined organic layers were washed with saturated NH4Cl (aq) (20 mL) then saturated NaCl (aq) (20 mL), dried over Na2SO4, filtered, then concentrated. The residue was purified by silica gel chromatography eluting with 2% EtOAc/petroleum ether to afford the title compound: 1H NMR (300 MHz, CD3OD) δ 7.98-8.02 (m, 2 H), 7.77-7.81 (m, 2 H), 7.38-7.44 (m, 2 H), 7.09-7.13 (m, 2 H), 3.91 (s, 3 H), 3.79-3.81 (m, 1 H), 3.34-3.40 (m, 1 H), 1.20-1.30 (m, 2 H), 1.03 (s, 9 H), 0.91-1.02 (m, 2 H), 0.68 (t, J=7.4 Hz, 3 H).

Workup

  1. stirringAfter stirring for 20 minutes
  2. extractionthe solution was extracted with CH2Cl2 (2×100 mL)
  3. washThe combined organic layers were washed with saturated NH4Cl (aq) (20 mL)
  4. dry with materialsaturated NaCl (aq) (20 mL), dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 2% EtOAc/petroleum ether

Sources & evidence

ORD record
ord-19c1705728d846b481cb5975f1b55607
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08324384B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes