Water → HCID 20384465, compound

HRID 1447660Notes

Reaction equation

[CH3:1][C:2]([OH:7])([CH:4]([CH3:6])[CH3:5])[CH3:3].C[Li].Cl[C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12].O>O1CCCC1.C(OCC)C>[C:11](=[O:12])([O:13][CH2:14][CH:15]=[CH2:16])[O:7][C:2]([CH3:3])([CH:4]([CH3:6])[CH3:5])[CH3:1]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 10.22 grams (0.10 mole) of 2,3-dimethylbutan-2-ol in 75 milliliters of anhydrous tetrahydrofuran at 0° C. was added one equivalent of methyllithium in diethyl ether, followed by 12.1 grams (0.10 mole) of allyl chloroformate in 25 milliliters of anhydrous tetrahydrofuran. During both additions the temperature was maintained at 0° C. After the last addition was complete the reaction mixture was stirred for about 18 hours and allowed to warm to ambient temperature. The reaction mixture was poured into water, and then extracted with ether. The ether solution was washed four times with water and dried over magnesium sulfate. Removal of solvent under reduced pressure yielded 16.45 grams (88.4% crude yield) of a light yellow oil. Distillation under vacuum provided three fractions.

Workup

additionAfter the last addition
temperatureto warm to ambient temperature
extractionextracted with ether
washThe ether solution was washed four times with water
dry with materialdried over magnesium sulfate
customRemoval of solvent under reduced pressure
customyielded 16.45 grams (88.4% crude yield) of a light yellow oil
distillationDistillation under vacuum
customprovided three fractions

Sources & evidence

ORD record: ord-d304cfda928f4de7b9d44abef2716cc8
Source dataset: uspto-grants-1979_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04177339

Reaction notes

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