Tin tetrachloride → HCID 23445625, compound

HRID 1067367Notes

Reaction equation

HRID 1067367 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][CH:40]=[CH:39][C:30]=1[CH2:31][C:32]1[O:33][C:34]([CH3:38])=[C:35]([CH3:37])[CH:36]=1>CN(C)C=O.C(Cl)Cl>[Br:28][C:29]1[CH:42]=[CH:41][CH:40]=[CH:39][C:30]=1[CH2:31][C:32]1[O:33][C:34]([CH3:38])=[C:35]([CH3:37])[C:36]=1[C:9]([C:8]1[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:7]=1)=[O:11]

Participants

7

Reactant 4

HCID 24287Tin tetrachlorideHCID 65578Oxalyl chlorideHCID 120939412-(2-Bromo-benzyl)4,5-dimethyl-furanHCID 15895034HCID 15895034, compound

Product 1

HCID 23445625HCID 23445625, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure in Example 5, step 2 using 3-cyclopentyl-p-anisic acid (2.00 g, 9.08 mmol, RN-59216-82-9), oxalyl chloride (0.871 mL, 9.99 mmol), N,N-dimethylformamide (2 drops), tin (IV) chloride (1.17 mL, 4.58 mmol) and 2-(2-bromo-benzyl)-4,5-dimethyl-furan (2.41 g, 9.08 mmol) in CH2Cl2. Purification on Biotage KP-Sil eluting with 4% EtOAc/pet. ether gave 2.82 g (66%) of the title compound as a clear oil. 1H NMR (DMSO-d6) δ1.40-1.44 (m, 2H), 1.57-1.73 (m, 4H), 1.79 (s, 3H), 1.87-1.93 (m, 2H), 2.16 (s, 3H), 3.21 (quintet, 1H), 3.86 (s, 3H), 3.93 (s, 2H), 7.04 (d, 1H), 7.11-7.18 (m, 2H), 7.29 (t, 1H), 7.51 (dd, 1H), 7.54-7.60 (m, 2H).

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-d9d90e68eef14d0d9a6384659584d054
Source dataset
uspto-grants-2001_06
Patent number
US06248764B1

Reaction notes

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