Methyl (3E)-4-phenyl-3-butenoate → (3E)-4-Phenyl-3-buten-1-ol

HRID 1005159Notes

Reaction equation

HRID 1005159 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[CH2:9][C:10](OC)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]1(/[CH:7]=[CH:8]/[CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 5370649Methyl (3E)-4-phenyl-3-butenoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 5370624(3E)-4-Phenyl-3-buten-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an analogous manner to that described in Example 5 (b), by reducing methyl (E)-4-phenyl-but-3-enoate by means of lithium aluminium hydride in tetrahydrofuran there was obtained (E)-4-phenyl-but-3-en-1-ol, which was converted into (E)-4-phenyl-but-3-enyl methanesulphonate in analogy to the procedure described in J.Chem.Soc. Perk.Trans. 1 (1988), (6), 1517-1519 for the preparation of the (Z) isomer.

Sources & evidence

ORD record
ord-16a348a886454436a10a87b2cb79139a
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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