Hexane → 1-Cyclopropyl-4,4-diethoxy-2-butyn-1-one
Reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[C:5]#[CH:6])[CH3:2].C([Li])CCC.CCCCCC.CON(C)[C:24]([CH:26]1[CH2:28][CH2:27]1)=[O:25]>C1COCC1>[CH:26]1([C:24](=[O:25])[C:6]#[C:5][CH:4]([O:7][CH2:8][CH3:9])[O:3][CH2:1][CH3:2])[CH2:28][CH2:27]1Participants
6
Conditions
- Temperature
- -70 °C
Procedure
3,3-Diethoxy-1-propyne (10 mL, 70 mmol) was dissolved under argon in THF (150 mL) and cooled to −70° C. Then a 1.6 M solution of n-butyllithium in hexane (48 mL, 77 mmol) was added slowly at −70° C., then allowed to warm to −30° C. and stirred at −30° C. for 30 min, then cooled again to −70° C. Cyclopropanecarboxylic acid methoxy-methyl-amide (10 g, 77 mmol) was added at once at −70° C. (the temperature rose to −50°) then stirred without cooling until 0° C. was reached, then quenched with sat. NH4Cl solution (20 mL). Extraction: 2×AcOEt, 1× sat. NH4Cl, 1× sat. NaCl. The crude brown oil (15 g) was purified by chromatography on silica gel in heptane/ethyl acetate 10:1. One obtained 6 g (43%) of a yellowish oil. MS: m/z=151(M).
Workup
- temperatureto warm to −30° C.
- temperaturecooled again to −70° C
- customrose to −50°
- stirringthen stirred
- temperaturewithout cooling until 0° C.
- customquenched with sat. NH4Cl solution (20 mL)
- extractionExtraction
- customThe crude brown oil (15 g) was purified by chromatography on silica gel in heptane/ethyl acetate 10:1
Sources & evidence
- ORD record
- ord-6e8c1b76083b43a18ceff5e97262da14
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07351700B2
Reaction notes
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