Tetrahydrofuran → 8-Vinyl-1,4-dioxaspiro[4,5]decane
Reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH2:13]1COCC1>>[CH:11]([CH:8]1[CH2:7][CH2:6][C:5]2([O:1][CH2:2][CH2:3][O:4]2)[CH2:10][CH2:9]1)=[CH2:13]Participants
Procedure
To a flask containing triphenylphosphonium bromide-sodamide complex (20.04 g, 48.10 mmol) was added THF (100 mL). After stirring @ rt for 1 hour, the solution was bright yellow (with some ppt). The r×n mixture was cooled to 0° C. and a solution of 1,4-dioxaspiro[4.5]decane-8-carbaldehyde (693 mg, 4.07 mmol, prepared as described in Pearson, et al. in J. Org. Chem. 1997, 62(16), 5284-5292) in THF (20 mL) was added dropwise via syringe. After the complete addition, the reaction mixture turned light peach and was stirred, warming to rt overnight. The reaction was quenched cautiously with saturated aq NaHCO3 at 0° C. and allowed to warm to room temperature, followed by water and extraction with ether. The concentrated organic layers were purified by flash chrom (silica gel, ether, stains PAA). To avoid losing some material on the rotovap (seems volatile), the bath temperature was kept under 35° C.
Workup
- additionTo a flask containing triphenylphosphonium bromide-sodamide complex (20.04 g, 48.10 mmol)
- temperatureThe r×n mixture was cooled to 0° C.
- additionAfter the complete addition
- stirringwas stirred
- temperaturewarming to rt overnight
- customThe reaction was quenched cautiously with saturated aq NaHCO3 at 0° C.
- temperatureto warm to room temperature
- extractionfollowed by water and extraction with ether
- customThe concentrated organic layers were purified by flash chrom (silica gel, ether, stains PAA)
- customwas kept under 35° C.
Sources & evidence
- ORD record
- ord-4c782dc7ac4f448687647bba1e94ca17
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518969B2
Reaction notes
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