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

HRID 2167025

Reaction equation

HRID 2167025 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-585200e88f9d4e65844a353c1dd6a01d
Source dataset
uspto-grants-2015_06
Patent number
US09044469B2

Linked notes

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