Oxalyl chloride → HCID 23445624, compound

HRID 1871334Notes

Reaction equation

HRID 1871334 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH2:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O)[CH3:2].C(Cl)(=O)C(Cl)=O.[Sn].[CH2:23]([C:30]1[O:31][C:32]([CH3:36])=[C:33]([CH3:35])[CH:34]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:23]([C:30]1[O:31][C:32]([CH3:36])=[C:33]([CH3:35])[C:34]=1[C:6]([C:5]1[CH:9]=[C:10]([CH2:14][CH3:15])[C:11]([O:12][CH3:13])=[C:3]([CH2:1][CH3:2])[CH:4]=1)=[O:8])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 5352426Tin atomHCID 15895031HCID 15895031, compoundHCID 234456633.5-Diethyl-4-methoxybenzoic acid

Product 1

HCID 23445624HCID 23445624, compound

Procedure

The title compound was prepared according to the procedure in Example 5, step 2, using 3,5-diethyl-4-methoxybenzoic acid (10.66 g, 51.3 mmol), oxalyl chloride (4.90 mL, 56.3 mmol), N,N-DMF (2 drops), tin IV chloride (6.60 mL, 56.3 mmol) and 2-benzyl-4,5-dimethylfuran (11.4 g, 61.3 mmol) to give 22.0 g, of the title compound. 1H NMR δ 1.13 (t, 6 H), 1.83 (s, 3 H), 2.19 (s, 3 H), 2.61 (q, 4 H), 3.74 (s, 3 H), 3.82 (s, 2 H), 7.05 (d, 2 H), 7.23-7.27 (m, 3 H), 7.42 (s, 2 H). mass spectrum (EI), m/z 376 (M+).

Workup

  1. customThe title compound was prepared
  2. customto give 22.0 g

Sources & evidence

ORD record
ord-6d4730d51d0446a4b94052b15f2213e7
Source dataset
uspto-grants-2000_08
Patent number
US06103708

Reaction notes

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