HCID 11260630, compound → HCID 23245531, compound

HRID 2304855Notes

Reaction equation

HRID 2304855 reaction equation
C([O:3][C:4](=O)/[CH:5]=[CH:6]/[CH2:7][CH2:8][CH2:9][C:10]([CH3:32])([CH3:31])[CH2:11]/[CH:12]=[CH:13]\[C:14]([O:23][Si:24]([CH2:29][CH3:30])([CH2:27][CH3:28])[CH2:25][CH3:26])([C:19]([F:22])([F:21])[F:20])[C:15]([F:18])([F:17])[F:16])C.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[F:18][C:15]([F:16])([F:17])[C:14]([O:23][Si:24]([CH2:29][CH3:30])([CH2:27][CH3:28])[CH2:25][CH3:26])([C:19]([F:21])([F:22])[F:20])/[CH:13]=[CH:12]\[CH2:11][C:10]([CH3:31])([CH3:32])[CH2:9][CH2:8][CH2:7]/[CH:6]=[CH:5]/[CH2:4][OH:3]

Participants

4

Reactant 2

HCID 11260630HCID 11260630, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 23245531HCID 23245531, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 10.09 g of (2E,9Z)-12,12,12-Trifluoro-7,7-dimethyl-11-triethylsilanyloxy-11-trifluoromethyl-dodeca-2,9-dienoic acid ethyl ester in 100 ml of toluene was added at −78° 40.0 ml of diisobutylaluminiumhydride (1.2 M in toluene) and stirring was continued for 30 min after which time t.l.c. indicated completion of the reaction. The mixture was washed with sat. aqueous NH4Cl-solution and water, the organic layer was dried over MgSO4 and evaporated to give 8.92 g of the pure (t.l.c.) title compound as a pale yellow oil. IR (neat): 3332m, br. (OH), 1669w (C═C).

Workup

  1. customcompletion of the reaction
  2. washThe mixture was washed with sat. aqueous NH4Cl-solution and water
  3. dry with materialthe organic layer was dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-8ba7e9135fab42e39a4217215513f172
Source dataset
uspto-grants-2002_08
Patent number
US06437142B1

Reaction notes

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