Tetrahydrofuran → 3-(2',4'-Difluoro-4-biphenylyl)butane-1,3-diol

HRID 26944Notes

Reaction equation

HRID 26944 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])=[CH:11][CH:10]=1)([OH:8])[CH3:7])C.C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>O.C(OCC)(=O)C>[F:22][C:16]1[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:15]=1[C:12]1[CH:13]=[CH:14][C:9]([C:6]([OH:8])([CH3:7])[CH2:5][CH2:4][OH:3])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 538342513-(2',4'-Difluoro-4-biphenylyl)-3-hydroxybutyric acid ethyl ester

Product 1

HCID 213225623-(2',4'-Difluoro-4-biphenylyl)butane-1,3-diol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 32 g. of 3-(2',4'-difluoro-4-biphenylyl)-3-hydroxybutyric acid ethyl ester in 300 ml. of absolute THF is added dropwise, under nitrogen, to a suspension of 4.6 g. of LiAlH4 in 200 ml. of THF and the mixture is heated under reflux for one hour. After cooling, ethyl acetate, water and 32% sodium hydroxide solution are added and the mixture is worked up in the customary manner to give 3-(2',4'-difluoro-4-biphenylyl)butane-1,3-diol, m.p. 82°-84°.

Workup

  1. temperatureunder reflux for one hour
  2. temperatureAfter cooling

Sources & evidence

ORD record
ord-226f9c79dfce4dac9693709436aac917
Source dataset
uspto-grants-1979_04
Patent number
US04151302

Reaction notes

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