Chloride → HCID 23445624, compound

HRID 1841340Notes

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].[Cl-].[CH2:24]([C:31]1[O:32][C:33]([CH3:37])=[C:34]([CH3:36])[CH:35]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:24]([C:31]1[O:32][C:33]([CH3:37])=[C:34]([CH3:36])[C:35]=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:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

Reactant 5

HCID 312Chloride

HCID 65578Oxalyl chloride

HCID 5352426Tin atom

HCID 15895031HCID 15895031, compound

HCID 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 TV 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, 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

customThe title compound was prepared
customto give 22.0 g

Sources & evidence

ORD record: ord-bddd2e72b98449d58b291479a9653b64
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06683107B2

Reaction notes

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