Methyl 1-(4-(3-(tert-butoxy)-3-oxopropoxy)phenyl)cyclopropane-1-carboxylate → HCID 59129343, compound

HRID 1908376Notes

Reaction equation

HRID 1908376 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)=[O:4]>Cl>[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

3

Reactant 1

HCID 59129236Methyl 1-(4-(3-(tert-butoxy)-3-oxopropoxy)phenyl)cyclopropane-1-carboxylate

Product 1

HCID 59129343HCID 59129343, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1-[4-(2-tert-butoxycarbonyl-ethoxy)-phenyl]-cyclopropanecarboxylic methyl ester (6.3 g, 20 mmol) in HCl (20%, 200 mL) was heated at 110° C. for 1 h. After cooling to room temperature, the resulting mixture was filtered. The solid washed with water and dried under vacuum to give 1-[4-(2-carboxy-ethoxy)-phenyl]-cyclopropanecarboxylic methyl ester (5.0 g, 96%). 1H NMR (300 MHz, DMSO) δ 7.23-7.19 (m, 2H), 6.85-6.81 (m, 2H), 4.13 (t, J=6.0 Hz, 2H), 3.51 (s, 3H), 2.66 (t, J=6.0 Hz, 2H), 1.43-1.39 (m, 2H), 1.14-1.10 (m, 2H).

Workup

  1. filtrationthe resulting mixture was filtered
  2. washThe solid washed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-76994ed3722343ddb6d49eeaa1a1102e
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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