Ethyl 2-(2-(4-(benzyloxy)-3,5-difluorophenyl)cyclopropyl)acetate → Ethyl 2-(2-(3,5-difluoro-4-hydroxyphenyl)cyclopropyl)acetate

HRID 1876360Notes

Reaction equation

HRID 1876360 reaction equation
C([O:8][C:9]1[C:14]([F:15])=[CH:13][C:12]([CH:16]2[CH2:18][CH:17]2[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:11][C:10]=1[F:25])C1C=CC=CC=1>CCOC(C)=O.CCO.[Pd]>[F:15][C:14]1[CH:13]=[C:12]([CH:16]2[CH2:18][CH:17]2[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:11]=[C:10]([F:25])[C:9]=1[OH:8]

Participants

4

Reactant 1

HCID 59455542Ethyl 2-(2-(4-(benzyloxy)-3,5-difluorophenyl)cyclopropyl)acetate

Product 1

HCID 58566498Ethyl 2-(2-(3,5-difluoro-4-hydroxyphenyl)cyclopropyl)acetateYield 88.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of ethyl 2-(2-(4-(benzyloxy)-3,5-difluorophenyl)cyclopropyl)acetate (505) (0.782 g, 2.25 mmol) in EtOAc/EtOH (5 mL/10 mL) was added 159 mg of 10% Pd/C, and the mixture was stirred under a hydrogen balloon overnight. After filtration through celite and washing with EtOH, the filtrate was concentrated in vacuo to afford 0.508 g of desired product (506) as a pale-yellow liquid. The product was sufficiently pure to be used directly in subsequent couplings. 1H NMR (400 MHz, CDCl3) δ: 6.67 (d, J=8.4 Hz, 2H), 4.96 (br, 1H), 4.23-4.05 (m, 2H), 2.50-2.26 (m, 2H), 1.70-1.66 (m, 1H), 1.33-1.19 (m, 4H), 0.97-0.79 (m, 2H).

Workup

  1. filtrationAfter filtration through celite
  2. washwashing with EtOH
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f1d8b626ee7a43b6958df81b599b00db
Source dataset
uspto-grants-2012_11
Patent number
US08309600B2

Reaction notes

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