Sodium hydride → 1-[1-(2,2-Diethoxyethoxyl)but-3-en-1-yl]-1-methylcyclopropane
Reaction equation
[CH3:1][C:2]1([CH:5]([OH:9])[CH2:6][CH:7]=[CH2:8])[CH2:4][CH2:3]1.[H-].[Na+].Br[CH2:13][CH:14]([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17]>O1CCCC1>[CH2:16]([O:15][CH:14]([O:18][CH2:19][CH3:20])[CH2:13][O:9][CH:5]([C:2]1([CH3:1])[CH2:4][CH2:3]1)[CH2:6][CH:7]=[CH2:8])[CH3:17]Participants
Procedure
A solution of 1-(1-methylcyclopropyl)but-3-en-1-ol (C52) (6.0 g, 47.6 mmol) in tetrahydrofuran (50 mL) was added to a 0° C. suspension of sodium hydride (60% in mineral oil, 7.7 g, 190.5 mmol) in tetrahydrofuran (200 mL). After stirring at room temperature for 10 minutes, 2-bromo-1,1-diethoxyethane (97%, 37.5 g, 190.5 mmol) was added drop-wise at room temperature. The reaction mixture was heated to 75° C. for 24 hours. It was then cooled to 0° C., slowly quenched with water (200 mL) and extracted with dichloromethane (3×500 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo; purification via silica gel chromatography (Gradient: 0% to 10% ethyl acetate in petroleum ether) afforded the product as a yellow oil.
Workup
- temperatureThe reaction mixture was heated to 75° C. for 24 hours
- temperatureIt was then cooled to 0° C.
- customslowly quenched with water (200 mL)
- extractionextracted with dichloromethane (3×500 mL)
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- custompurification via silica gel chromatography (Gradient: 0% to 10% ethyl acetate in petroleum ether)
Sources & evidence
- ORD record
- ord-a54f2c208f9645529e205ff354ec9d39
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09403846B2
Reaction notes
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