Water → HCID 18617744, compound

HRID 1264232Notes

Reaction equation

HRID 1264232 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[O:20][CH:21]=[CH:22][CH:23]=2)=[CH:15][CH:14]=1)([CH3:12])[CH3:11].O.[OH-].[Na+]>C1COCC1.CCOCC>[O:20]1[CH:21]=[CH:22][CH:23]=[C:19]1[C:16]1[CH:17]=[CH:18][C:13]([C:10]([CH3:12])([CH3:11])[CH2:9][OH:8])=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21350305HCID 21350305, compound

Product 1

HCID 18617744HCID 18617744, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled solution (0° C.) of (1M)lithium aluminum hydride (13.3 mL, 13.3 mmol) in THF (27 mL) is added a solution of 2-(4-furan-2-yl-phenyl)-2-propionic acid methyl ester (3.1 g, 12.7 mmol) (reference example 30a) in THF (11 mL). The resulting solution is stirred for 15 min then added slowly H2O (0.5 mL), 15% NaOH (0.5 mL) and H2O (1.5 mL). The resulting slurry is diluted with ether, filtered through a pad of celite and the filtrate concentrated to give 2.7 g of title compound as a white crystalline solid. 1H NMR (CDCl3) δ 1.34 (s, 6H), 3.62 (m, 3H), 6.46 (m, 1H), 6.62 (d, J=3 Hz, 1H), 7.40 (d, J=8 Hz, 2H), 7.46 (bs, 1H), 7.64 (d, J=8 Hz, 2H). MS (EI) m/z 216 (M+).

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-eb02dcf1a58b41cab6f00296fa013e4c
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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