HCID 21193478, compound → HCID 9924853, compound

HRID 1954281Notes

Reaction equation

HRID 1954281 reaction equation
[CH2:1]([C:8]1[O:9][C:10]([CH3:29])=[C:11]([CH3:28])[C:12]=1[C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21]C)=[C:17]([CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[CH:16]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl>[CH3:29][C:10]1[O:9][C:8]2[CH:1]=[C:2]3[C:3](=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([CH:23]5[CH2:27][CH2:26][CH2:25][CH2:24]5)[CH:16]=4)[C:12]=2[C:11]=1[CH3:28])[CH:4]=[CH:5][CH:6]=[CH:7]3

Participants

3

Reactant 1

HCID 21193478HCID 21193478, compound

Product 1

HCID 9924853HCID 9924853, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure in Example 1, step 5 using (2-benzyl-4,5-dimethyl-furan-3-yl)-(3-cyclopentyl-4-methoxy-phenyl)-methanone (18.8 g, 48.4 mmol) boron tribromide (34.8 mL, 0.367 mol) in CH2Cl2. Purification on silica gel eluting with a 2, 5, 10 and 20% EtOAc/hexane step gradient gave 1.55 g (10%) of the title compound. 1H NMR (DMSO-d6)δ 1.56-1.69 (m, 9 H), 1.96-1.97 (m, 5 H), 2.37 (s, 3 H), 3.33 (q, 1 H, masked by H2O), 6.91-7.00 (m, 2 H), 7.06 (d, 1 H), 7.30 (t, 1 H), 7.41 (t, 1 H), 7.56 (d, 1 H), 7.91 (s, 1 H), 7.98 (d, 1 H), 9.48 (s, 1 H).

Workup

  1. customThe title compound was prepared
  2. customPurification on silica gel eluting with a 2, 5, 10 and 20% EtOAc/hexane step gradient

Sources & evidence

ORD record
ord-f56fa14242014272915faa09f938f1b6
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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