Hexane → HCID 22226108, compound
Reaction equation
[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.[CH2:17]([O:20][C:21]1[C:22](/[C:35](/[CH2:43][CH3:44])=[C:36](/[F:42])\[C:37](OCC)=[O:38])=[CH:23][C:24]2[C:25]([CH3:34])([CH3:33])[CH2:26][CH2:27][C:28]([CH3:32])([CH3:31])[C:29]=2[CH:30]=1)[CH2:18][CH3:19]>C1COCC1>[CH2:17]([O:20][C:21]1[C:22](/[C:35](/[CH2:43][CH3:44])=[C:36](/[F:42])\[CH2:37][OH:38])=[CH:23][C:24]2[C:25]([CH3:33])([CH3:34])[CH2:26][CH2:27][C:28]([CH3:32])([CH3:31])[C:29]=2[CH:30]=1)[CH2:18][CH3:19]Participants
Conditions
- Temperature
- -78 °C
Procedure
A solution of diisobutylaluminum hydride and hexane (40 mL, 1 M, 40 mmol) was added to a stirring solution of ethyl (E)-3-(3-n-propoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2-fluoropent-2-enoate (Intermediate 8, 3.52 g, 9.36 mmol) in THF (60 mL) at −78° C. under argon. The solution was stirred at −78° C. for 3 h, and the reaction was quenched at −78° C. by adding methanol. The solution was warmed to room temperature and stirred for 1.5 h. The solution was treated with 1 M aqueous HCl, and the products were extracted three times with ether. The combined organic layers were washed with water, brine and dried over magnesium sulfate. The solvent was removed in vacuo to give the title compound after purification by silica gel chromatography (15% ethyl acetate in hexane).
Workup
- customthe reaction was quenched at −78° C.
- additionby adding methanol
- temperatureThe solution was warmed to room temperature
- stirringstirred for 1.5 h
- additionThe solution was treated with 1 M aqueous HCl
- extractionthe products were extracted three times with ether
- washThe combined organic layers were washed with water, brine
- dry with materialdried over magnesium sulfate
- customThe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-e3151f77ef8147949ba5296e949ae547
- Source dataset
- uspto-grants-2006_03
- Patent number
- US07019034B2
Reaction notes
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