Hydrochloric Acid → (E)-3-(4'-chloro-biphenyl-4-yl)-but-2-en-1-ol

HRID 984317Notes

Reaction equation

HRID 984317 reaction equation
CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.C([O:19][C:20](=O)/[CH:21]=[C:22](/[C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)=[CH:26][CH:25]=1)\[CH3:23])C.Cl>C1COCC1.CO>[Cl:36][C:33]1[CH:32]=[CH:31][C:30]([C:27]2[CH:28]=[CH:29][C:24](/[C:22](/[CH3:23])=[CH:21]/[CH2:20][OH:19])=[CH:25][CH:26]=2)=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 22557604(E)-ethyl-3-(4'-chloro-biphenyl-4-yl)-but-2-enoate

Product 1

HCID 69800319(E)-3-(4'-chloro-biphenyl-4-yl)-but-2-en-1-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 1M solution of DIBAL-H in toluene (10 ml, 10 mmol) was added dropwise, at −70° C. over 10 min, to a stirred solution of (E)-ethyl-3-(4′-chloro-biphenyl-4-yl)-but-2-enoate (1.0 g, 3.32 mmol) in dry THF (25 ml), and the mixture warmed to room temperature over 4 h. Methanol (1 ml) was carefully added, followed by 1N HCl (50 ml) and the resulting mixture extracted with ethyl acetate (2×50 ml). The combined organic extracts were washed with brine, dried (MgSO4), and evaporated to give the product, (E)-3-(4′-chloro-biphenyl-4-yl)-but-2-en-1-ol as a colourless solid: 0.86 g (100%).

Workup

  1. extractionthe resulting mixture extracted with ethyl acetate (2×50 ml)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-0217c3520fea411787e302516070fa3f
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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