Water → HCID 15840342, compound

HRID 1935643Notes

Reaction equation

C([Li])(CC)C.[O:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH:11]1[O:16][CH2:15][CH2:14][CH2:13][O:12]1.[CH2:17]([Sn:21](Cl)([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH3:20].O>C1COCC1>[O:16]1[CH2:15][CH2:14][CH2:13][O:12][CH:11]1[C:7]1[O:6][C:10]([Sn:21]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:9][CH:8]=1

Participants

Conditions

Temperature: -20 °C

Procedure

200 ml of sec-butyllithium (1.3M solution in cyclohexane, 260 mmol) were added dropwise to a solution of 34.4 g of 2-(2-furyl)-1,3-dioxane (224 mmol, obtainable from furfural and propane-1,3-diol) in 320 ml of THF at −70° C. in the course of 20 minutes. The solution was warmed at −20° C. for 30 minutes and then cooled again to −78° C. A solution of 60.8 ml of tributylstannyl chloride in 160 ml of THF was then added dropwise in the course of 30 minutes, after which the mixture was allowed to warm to room temperature. After 2.5 hours, water was added and the mixture was extracted with ethyl acetate. The organic phase was dried with magnesium sulphate and concentrated and the residue was distilled (boiling point0.8 180° C.). 93 g were obtained.

Workup

temperaturecooled again to −78° C
temperatureto warm to room temperature
extractionthe mixture was extracted with ethyl acetate
dry with materialThe organic phase was dried with magnesium sulphate
concentrationconcentrated
distillationthe residue was distilled (boiling point0.8 180° C.)
custom93 g were obtained

Sources & evidence

ORD record: ord-66a5d2e4b4a4495898a606e8b224c950
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06387940B1

Reaction notes

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