Hydrogen Peroxide → HCID 22011254, compound

HRID 322623Notes

Reaction equation

HRID 322623 reaction equation
ClCCl.[O:4]1[CH2:8][CH2:7][O:6][CH:5]1[CH:9]([CH2:13][CH2:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:10][CH:11]=[CH2:12].[OH-:23].[Na+].OO>CCCCCC.O.C(O)C>[O:4]1[CH2:8][CH2:7][O:6][CH:5]1[CH:9]([CH2:13][CH2:14][O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:10][CH2:11][CH2:12][OH:23]

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 10999869HCID 10999869, compound

Product 1

HCID 22011254HCID 22011254, compoundYield 74.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

A 1 M solution of borane-methyl sulfide complex in dichloromethane (27 mL, 27 mmol) was added dropwise to a stirred solution of the olefin 14 (21 g, 80.36 mmol), prepared according to Example 12, in hexane (60 mL) at 0° C. The mixture was stirred for 3 h at room temperature, then cooled to 0° C., and then absolute ethanol (15 mL) was added dropwise, followed by 15% NaOH (15 mL) and 30% H2O2 (15 mL). The reaction mixture was heated at reflux for 1 h. cooled to room temperature, and poured into water (200 mL). The organic layer was separated, and the aqueous layer was extracted with ether (3×75 mL). The organic layers were combined, dried over MgSO4, and concentrated under reduced pressure. The crude product was chromatographed on a silica gel column, eluting with 2% methanol in ether, to give the alcohol 15 (16.8 g, 74.6%) as a viscous liquid. IR (KBr)νmax 3442, 3034, 2952, 2878, 1458, 1407, 1364, 1206, 1103, 846, 742, 698 cm−1; 1HNMR (CDCl3) δ 1.36-1.39 (m, 1 H), 1.53-1.64 (m, 4 H), 1.79-1.90 (m, 3 H), 3.53-3.59 (m, 4 H), 3.79-3.92 (m, 4 H), 4.49 (s, 2H), 4.78 (d, J=3.6 Hz, 1 H), 7.25-7.32 (m, 5 H); 13CNMR (CDCl3) δ 25.38, 29.23, 30.17, 38.19, 62.76, 64.78, 64.84, 68.52, 72.72, 106.49, 127.39, 127.56, 128.23, 138.54: mass spectrum (EI), m/z (rel intensity) 280 (M+.0.02), 235(2.1), 220 (14), 219 (84), 218 (69), 172 (15), 146 (23), 127 (15), 91 (35), 84 (9), 73 (10), 65 (5.5).

Workup

  1. customprepared
  2. temperaturecooled to 0° C.
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 1 h.
  5. temperaturecooled to room temperature
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with ether (3×75 mL)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was chromatographed on a silica gel column
  11. washeluting with 2% methanol in ether

Sources & evidence

ORD record
ord-490468e0739f46f688f477d69f0fceea
Source dataset
uspto-grants-2001_04
Patent number
US06211360B1

Reaction notes

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