Water → HCID 20384467, compound

HRID 838790Notes

Reaction equation

HRID 838790 reaction equation
[CH3:1][CH:2]([C:4]([CH3:8])([OH:7])[CH2:5][CH3:6])[CH3:3].C[Li].Cl[C:12]([O:14][CH2:15][C:16](=[CH2:18])[CH3:17])=[O:13].O>O1CCCC1.C(OCC)C>[C:12](=[O:13])([O:14][CH2:15][C:16](=[CH2:17])[CH3:18])[O:7][C:4]([CH3:8])([CH2:5][CH3:6])[CH:2]([CH3:3])[CH3:1]

Participants

7

Reactant 4

HCID 962WaterHCID 116852,3-Dimethylpentan-3-olHCID 170604Carbonochloridic acid, 2-methyl-2-propen-1-yl esterHCID 178418348HCID 178418348, compound

Product 1

HCID 20384467HCID 20384467, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 13.94 grams (0.12 mole) of 2,3-dimethylpentan-3-ol in 75 milliliters of anhydrous tetrahydrofuran at 0° C under a nitrogen atmosphere was added with stirring one equivalent of methyllithium in diethyl ether. Then 19.31 grams (0.14 mole) of methallyl chloroformate in 25 milliliters of anhydrous tetrahydrofuran was added. During additions the temperature was maintained at 0° C. Cooling was discontinued and the reaction mixture was stirred for about 18 hours. The reaction mixture was poured into water, and then extracted with ether. The ether layer was separated and washed with water, and then dried over magnesium sulfate. Removal of solvent under reduced pressure yielded 24.32 grams (94.6%) of a yellow oil. A pure sample was obtained by vacuum distillation (Fraction 2).

Workup

  1. temperatureCooling
  2. extractionextracted with ether
  3. customThe ether layer was separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-627e7d89d7424008841fee1e77b588c0
Source dataset
uspto-grants-1978_06
Patent number
US04092988

Reaction notes

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