Methyl chloroformate → Ethyl 3-(3-cyclopentyl-4-methoxycarbonyloxy-phenyl)propanoate

HRID 383381Notes

Reaction equation

HRID 383381 reaction equation
[CH:1]1([C:6]2[CH:7]=[C:8]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=[CH:10][C:11]=2[OH:12])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:28]([O:30][CH3:31])=[O:29]>ClCCl>[CH:1]1([C:6]2[CH:7]=[C:8]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=[CH:10][C:11]=2[O:12][C:28]([O:30][CH3:31])=[O:29])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 59394986Ethyl 3-(3-cyclopentyl-4-hydroxy-phenyl)propanoate

Product 1

HCID 59395019Ethyl 3-(3-cyclopentyl-4-methoxycarbonyloxy-phenyl)propanoateYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3-(3-cyclopentyl-4-hydroxy-phenyl)propanoate (857 mg, 3.27 mmol) and triethylamine (911 μL, 6.53 mmol) in dichloromethane (5 mL) under a N2 atmosphere at 0° C. was added methyl chloroformate (463 mg, 377 μL, 4.90 mmol) dropwise. After 1 h, the reaction mixture was partitioned between dichloromethane/water, separated and the aqueous layer was extracted once more with dichloromethane. The combined organics were dried over Na2SO4, filtered and concentrated. Purification by silica gel chromatography (0-30% ethyl acetate/hexanes) provided ethyl 3-(3-cyclopentyl-4-methoxycarbonyloxy-phenyl)propanoate (920 mg, 88% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 7.20 (d, J=1.7 Hz, 1H), 7.09-7.03 (m, 2H), 4.04 (q, J=7.1 Hz, 2H), 3.82 (s, 3H), 3.03-2.96 (m, 1H), 2.83 (t, J=7.6 Hz, 2H), 2.61 (t, J=7.6 Hz, 2H), 1.93-1.86 (m, 2H), 1.77-1.72 (m, 2H), 1.66-1.58 (m, 2H), 1.54-1.47 (m, 2H), 1.15 (t, J=7.1 Hz, 3H).

Workup

  1. customthe reaction mixture was partitioned between dichloromethane/water
  2. customseparated
  3. extractionthe aqueous layer was extracted once more with dichloromethane
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (0-30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2354595a8b1f42a986602dce5ab70738
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

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