Oxalyl chloride → HCID 23445624, compound

HRID 1067361Notes

Reaction equation

HRID 1067361 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 δ1.13 (t, 6H), 1.83 (s, 3H), 2.19 (s, 3H), 2.61 (q, 4H), 3.74 (s, 3H), 3.82 (s, 2H), 7.05 (d, 2H), 7.23-7.27 (m, 3H), 7.42 (s, 2H). 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-c3d08b1ee743495d8db61d4fa1939c14
Source dataset
uspto-grants-2001_06
Patent number
US06248764B1

Reaction notes

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