Boron trifluoride etherate → 2,2-Dimethyl-4-(4-methylphenyl)-4-(prop-2-en-1-yl)oxane

HRID 76219

Reaction equation

HRID 76219 reaction equation
[CH2:1]([Si](C)(C)C)[CH:2]=[CH2:3].[CH3:8][C:9]1([CH3:23])[CH2:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(O)[CH2:12][CH2:11][O:10]1.B(F)(F)F.O(CC)CC>C(Cl)Cl>[CH3:8][C:9]1([CH3:23])[CH2:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)([CH2:3][CH:2]=[CH2:1])[CH2:12][CH2:11][O:10]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 69808AllyltrimethylsilaneHCID 641378172,2-Dimethyl-4-(4-methylphenyl)oxan-4-ol

Product 1

HCID 683142852,2-Dimethyl-4-(4-methylphenyl)-4-(prop-2-en-1-yl)oxane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Allyltrimethylsilane (4.34 ml, 27.2 mmol) was added to a solution of 2,2-dimethyl-4-(4-methylphenyl)oxan-4-ol (3.0 g, 13.6 mmol) in dry CH2Cl2 (100 ml) at 0° C., followed by BF3—OEt2 (3.42 ml, 27.2 mmol). The resulting mix was stirred at 0° C. for 1 h. The reaction was quenched with H2O (10 ml) and diluted with CH2Cl2 (10 ml), and washed with sat. NaHCO3 (20 ml), brine (20 ml), dried and concentrated. Purified by normal phase SiO2 chromatography (5 to 40% EtOAc/hexanes) to give 2,2-dimethyl-4-(4-methylphenyl)-4-(prop-2-en-1-yl)oxane as a colorless oil, which was used crude (2.49 g, 75%).

Workup

  1. additionThe resulting mix
  2. customThe reaction was quenched with H2O (10 ml)
  3. additiondiluted with CH2Cl2 (10 ml)
  4. washwashed with sat. NaHCO3 (20 ml), brine (20 ml)
  5. customdried
  6. concentrationconcentrated
  7. customPurified by normal phase SiO2 chromatography (5 to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4194aaae1920413e9a917b02d374f89a
Source dataset
uspto-grants-2014_09
Patent number
US08835488B2

Linked notes

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