Butanoic acid, 4-chloro-, 1,1-dimethylethyl ester → 3-[(tert-Butyl)oxycarbonyl]propyl phenylmethyl butane-1,4-dioate

HRID 130597Notes

Reaction equation

HRID 130597 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[CH2:12]([O:19][C:20](=[O:26])[CH2:21][CH2:22][C:23]([O-:25])=[O:24])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cs+]>CN(C=O)C>[C:23]([O:25][CH2:2][CH2:3][CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])(=[O:24])[CH2:22][CH2:21][C:20]([O:19][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:26]

Participants

4

Reactant 2

HCID 527695Butanoic acid, 4-chloro-, 1,1-dimethylethyl esterHCID 86600772Cesium monobenzylsuccinate

Product 1

HCID 597306963-[(tert-Butyl)oxycarbonyl]propyl phenylmethyl butane-1,4-dioateYield 14.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl 4-chlorobutyrate (8.9 g, 50 mmol) and cesium monobenzylsuccinate (prepared from monobenzyl succinate and CsOH) (50 mmol) in 100 mL of DMF was heated at 80° C. for 2 days. DMF was evaporated and chromatographed on silica (hexane-ethyl acetate) to afford 2.5 g (14%) of the title compound 3 as a colorless liquid. 1H NMR (DMSO-d6) δ 7.35 (s, 5H), 5.09 (s, 2H), 3.99 (t, J=7 Hz, 2H), 2.58 (m, 4H), 2.25 (t, J=7 Hz, 2H), 1.93 (q, 2H), 1.41 (s, 9H).

Workup

  1. customDMF was evaporated
  2. customchromatographed on silica (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-af1e4825cede4c4e89a35d132e5d952e
Source dataset
uspto-grants-2008_06
Patent number
US07381818B2

Reaction notes

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