Hydrochloric Acid → HCID 18651184, compound

HRID 1590404Notes

Reaction equation

HRID 1590404 reaction equation
C([O:3][C:4](=O)/[C:5](/[F:20])=[C:6](/[C@@H:9]1[CH2:11][C@H:10]1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)\CC)C.[H-].C([Al+]CC(C)C)C(C)C.Cl>ClCCl>[Cl:19][C:14]1[CH:13]=[C:12]([C@@H:10]2[CH2:11][C@H:9]2/[CH:6]=[C:5](\[F:20])/[CH2:4][OH:3])[CH:17]=[CH:16][C:15]=1[Cl:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 18651189HCID 18651189, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 18651184HCID 18651184, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above ester (4 g) was dissolved in dichloromethane (30 ml) and cooled to -20° under nitrogen. Diisobutylaluminium hydride (26 ml) was added dropwise. After 18 hours at 25° dilate hydrochloric acid was carefully added and the mixture worked up in the usual manner to give (±)-(2Z)-3-[trans-2-(3,4-dichlorophenyl)cyclopropyl]-2-fluoroprop-2-en-1-ol (3.3 g). NMR 1H: 7.32(1H,d), 7.17(1H,d), 6.90(1H,dd), 4.10(2H,dd), 3.60(1H,t), 1.90(2H,m), 1.20(2H,m).

Workup

  1. temperaturecooled to -20° under nitrogen

Sources & evidence

ORD record
ord-e804c7cae1b345cfa7589915e70699d8
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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