Tin tetrachloride → [2-(4-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3-cyclopentyl-4-methoxy-phenyl)-methanone

HRID 1841325Notes

Reaction equation

HRID 1841325 reaction equation
[CH:1]1([C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[C:9]([OH:11])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.[Sn](Cl)(Cl)(Cl)Cl.[Br:28][C:29]1[CH:42]=[CH:41][C:32]([CH2:33][C:34]2[O:35][C:36]([CH3:40])=[C:37]([CH3:39])[CH:38]=2)=[CH:31][CH:30]=1>CN(C)C=O>[Br:28][C:29]1[CH:42]=[CH:41][C:32]([CH2:33][C:34]2[O:35][C:36]([CH3:40])=[C:37]([CH3:39])[C:38]=2[C:9]([C:8]2[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:6]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:7]=2)=[O:11])=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 24287Tin tetrachlorideHCID 65578Oxalyl chlorideHCID 158950343-Cyclopentyl-p-anisic acidHCID 234456202-(4-Bromo-benzyl)-4,5-dimethyl-furan

Product 1

HCID 23445643[2-(4-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3-cyclopentyl-4-methoxy-phenyl)-methanoneYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

The title compound was prepared according to the procedure in Example 5, step 2 using 3-cyclopentyl-p-anisic acid (2.04 g, 9.24 mmol, RN-59216-82-9), oxalyl chloride (0.887 mL, 10.2 mmol), N,N-dimethylformamide (2 drops), tin (IV) chloride (1.19 mL, 10.2 mmol) and 2-(4-bromo-benzyl)-4,5-dimethyl-furan (2.45 g, 9.24 mmol) in CH2C2. Purification on Biotage KP-Sil eluting with 4% EtOAc/pet. ether gave 3.39 g (78%) of the title compound. 1H NMR (DMSO-d6) δ1.38-1.47 (m, 2 H), 1.60-1.73 (m, 4 H), 1.79 (s, 3 H), 1.90-1.94 (m, 2 H), 2.18 (s, 3 H), 3.21 (quintet, 1 H) 3.82 (s, 2 H), 3.88 (s, 3 H), 7.02-7.08 (m, 3 H), 7.44 (d, 2 H), 7.55-7.61 (m , 2 H).

Workup

  1. customThe title compound was prepared
  2. customPurification on Biotage KP-Sil
  3. washeluting with 4% EtOAc/pet. ether

Sources & evidence

ORD record
ord-d136d5aa4bdf4b60bef92b99a27b4ae0
Source dataset
uspto-grants-2004_01
Patent number
US06683107B2

Reaction notes

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