Hydrogen Peroxide → HCID 57691440, compound

HRID 1867649Notes

Reaction equation

HRID 1867649 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:6][O:7][CH2:8][C:9]1([CH:19]=[CH2:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][O:10]1.B1C2CCCC1CCC2.[OH-:39].[Na+].OO>>[F:29][C:2]([F:28])([F:1])[C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:6][O:7][CH2:8][C:9]1([CH2:19][CH2:20][OH:39])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][O:10]1

Participants

5

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 57691442HCID 57691442, compound

Product 1

HCID 57691440HCID 57691440, compound

Procedure

1-((3,5-Bis(trifluoromethyl)benzyloxy)methyl)-1-vinylisochroman (125 mg, 0.300 mmol) was dissolved in 9-BBN (0.5 M in tetrahydrofuran, 2.4 mL, 1.2 mmol) and stirred overnight at room temperature. The reaction was cooled to 0° C. and treated with 4 M sodium hydroxide (1 mL) and then 30% hydrogen peroxide (1 mL) dropwise. The reaction was stirred at 0° C. for 1 h and then quenched by addition of saturated ammonium chloride. The mixture was extracted with diethyl ether (2×) which was washed with brine, dried over magnesium sulfate, and purified by column chromatography (25%-->37% EtOAc/Hex) to give 125 mg (96%) as a colorless oil. 1H-NMR (CDCl3, 300 MHz) δ 7.77 (s, 1H), 7.70 (s, 2H), 7.05-7.25 (m, 4H), 4.67 (qAB, JAB=13.1 Hz, 2H), 4.03 (dd, J=7.3, 3.7 Hz, 2H), 3.78 (qAB, JAB=10.4 Hz, 2H), 3.61 (m, 2H), 2.99 (m, 1H), 2.72 (ddd, J=16.2, 3.4, 3.4 Hz, 1H), 2.62 (bs, 1H), 2.36 (m, 1H), 2.12 (ddd, J=15.0, 5.5, 4.6 Hz, 1H); 13C-NMR (CDCl3, 126 MHz) δ 141.1, 136.9, 134.8, 131.8 (q, J=33.6 Hz), 129.2, 127.3, 127.1, 126.6, 125.6, 123.4 (q, J=273 Hz), 121.6, 79.9, 76.4, 72.1, 60.7, 59.3, 39.9, 29.5. Mass spec.: 435.29 (MH)+.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. stirringThe reaction was stirred at 0° C. for 1 h
  3. customquenched by addition of saturated ammonium chloride
  4. extractionThe mixture was extracted with diethyl ether (2×) which
  5. washwas washed with brine
  6. dry with materialdried over magnesium sulfate
  7. custompurified by column chromatography (25%-->37% EtOAc/Hex)
  8. customto give 125 mg (96%) as a colorless oil

Sources & evidence

ORD record
ord-73770ac49a4e46c2bdcb6c9db523d722
Source dataset
uspto-grants-2009_12
Patent number
US07632861B2

Reaction notes

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