HCID 15895032, compound → (2-Benzyl-4,5-dimethyl-furan-3-yl)-(3,5-diisopropyl-4-hydroxy-phenyl)-methanone

HRID 1280876Notes

Reaction equation

HRID 1280876 reaction equation
[CH2:1]([C:8]1[O:9][C:10]([CH3:30])=[C:11]([CH3:29])[C:12]=1[C:13]([C:15]1[CH:20]=[C:19]([CH:21]([CH3:23])[CH3:22])[C:18]([O:24]C)=[C:17]([CH:26]([CH3:28])[CH3:27])[CH:16]=1)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.C(Cl)Cl.C(=O)=O.CC(C)=O>C(Cl)Cl>[CH2:1]([C:8]1[O:9][C:10]([CH3:30])=[C:11]([CH3:29])[C:12]=1[C:13]([C:15]1[CH:16]=[C:17]([CH:26]([CH3:27])[CH3:28])[C:18]([OH:24])=[C:19]([CH:21]([CH3:23])[CH3:22])[CH:20]=1)=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 15895032HCID 15895032, compoundHCID 18522661Acetone cardiceHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 15895033(2-Benzyl-4,5-dimethyl-furan-3-yl)-(3,5-diisopropyl-4-hydroxy-phenyl)-methanoneYield 50.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At −78° C., to a stirred solution of (2-benzyl-4,5-dimethyl-furan-3-yl)-(3,5-diisopropyl-4-methoxy-phenyl)-methanone (2.00 g, 4.94 mmol) in CH2Cl2 (16.6 mL) was added 1M boron tribromide/CH2Cl2 (10.4 mL). After the addition was complete, the dry ice/acetone bath was replaced with an ice bath and the reaction was stirred for 1.5 h. The reaction was quenched into crushed ice (18 g), diluted with H2O (20 mL) and extracted with ether. The combined ethereal extracts were washed with brine, dried (MgSO4) and concentrated. The crude product was purified on silica gel eluting with 15% acetone/hexane to give 0.97 g (50%) of the title compound as a white solid, mp 138° C.; 1H NMR (DMSO-d6) δ 1.14 (d, 12H), 1.80 (s, 3H), 2.19 (s, 3H), 3.34 [septet (under H2O peak), 2H], 3.84 (s, 2H), 7.04 (d, 2H), 7.17-7.25 (m, 3H), 7.44 (s, 2H), 9.11 (s, 1H). IR (KBr) 3400, 2950, 1580, 1320, 1200 cm−1. mass spectrum (EI), m/z 390 (M+). Anal. Calcd. for C26H30O3.0.2H2O: C, 79.24; H, 7.77; N, 0.12. Found: C, 79.27; H, 7.85; N, 0.12.

Workup

  1. additionAfter the addition
  2. customThe reaction was quenched
  3. custominto crushed ice (18 g)
  4. additiondiluted with H2O (20 mL)
  5. extractionextracted with ether
  6. washThe combined ethereal extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe crude product was purified on silica gel eluting with 15% acetone/hexane

Sources & evidence

ORD record
ord-f296637577224d81a5853c1927b2dc3b
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

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