Hydrogen Peroxide → HCID 18617820, compound

HRID 1264211Notes

Reaction equation

HRID 1264211 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)=[CH:8][CH:7]=1)([CH3:5])[CH:3]=[CH2:4].C1C[O:20]CC1.[OH-].[Na+].OO>CCOCC>[O:13]1[CH:14]=[CH:15][CH:16]=[C:12]1[C:9]1[CH:10]=[CH:11][C:6]([C:2]([CH3:1])([CH3:5])[CH2:3][CH2:4][OH:20])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 18617849HCID 18617849, compound

Product 1

HCID 18617820HCID 18617820, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

To a cooled solution (0° C.) of 2-[4-(1,1-dimethyl-allyl)-phenyl]-furan (424 mg, 2 mmol) (reference example 51)in THF (4 mL) is added dropwise (1M)borane-THF complex (2.2 mL, 2.2 mmol) and the resulting mixture stirred for 1 hour. To the mixture is added 10% NaOH (1.5 mL) and 30 wt % H2O2 (1.5 mL) and stirred for 1 hour while allowing to warm to 20° C. The mixture is diluted with ether, washed with water and brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 25% ethyl acetate in hexanes) to give 341 mg of the title compound. 1H NMR (CDCl3) δ 1.34 (s, 6H), 1.40 (m, 1H), 1.94 (t, J=8 Hz, 2H), 3.48 (t, J=8 Hz, 2H), 6.45 (m, 1H), 6.60 (m, 1H), 7.35 (d, J=8 Hz, 2H), 7.44 (bs, 1H), 6.61 (d, J=8 Hz, 2H). MS (EI) m/z 230 (M+).

Workup

  1. stirringstirred for 1 hour
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by flash chromatography (eluting with 25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c9ca72576ebc4163868c1012ab5f8cd0
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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