Aluminium lithium hydride → 2-(4-(Benzyloxy)-3-fluorophenyl)ethanol

HRID 2377936Notes

Reaction equation

HRID 2377936 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7]([F:19])[CH:6]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH2:12]([O:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][CH2:3][OH:2])=[CH:6][C:7]=1[F:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67205182(4-benzyloxy-3-fluoro-phenyl)-acetic Acid Methyl Ester

Product 1

HCID 672034892-(4-(Benzyloxy)-3-fluorophenyl)ethanolYield 82.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (4-benzyloxy-3-fluoro-phenyl)-acetic acid methyl ester (7.1 g, 25.7 mmol) in ether (150 mL), was LAH (1.07 g, 28.3 mmol) added portionwise at 0° C. The reaction mixture stirred for 2 hours at the same temperature. The reaction was quenched with H2O (5 mL) at 0° C. The solid material was filtrated off and washed with ether (50 mL). The ether was dried over MgSO4 and concentrated under vacuum to afford the desired compound (5.2 g, 82%) as a white solid. The crude compound was used for the next step without further purification. 1H NMR (400 Mz, DMSO-d6) δ 7.34-7.48 (m, 5H), 7.09-7.17 (m, 2H), 6.96-6.98 (m, 1H), 5.17 (s, 2H), 4.66 (s, 1H), 3.60 (b, 2H), 2.68 (m, 2H). LCMS 246.3 [MH+].

Workup

  1. additionadded portionwise at 0° C
  2. customThe reaction was quenched with H2O (5 mL) at 0° C
  3. filtrationThe solid material was filtrated off
  4. washwashed with ether (50 mL)
  5. dry with materialThe ether was dried over MgSO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-71c1bc5959dd4514ba5599539dbf4fb6
Source dataset
uspto-grants-2008_12
Patent number
US07470699B2

Reaction notes

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