Tin tetrachloride → HCID 18430717, compound

HRID 1954298Notes

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)(Cl)(Cl)Cl.[CH2:27]([C:34]1[S:35][C:36]([CH3:40])=[C:37]([CH3:39])[CH:38]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH2:27]([C:34]1[S:35][C:36]([CH3:40])=[C:37]([CH3:39])[C:38]=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:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

Reactant 4

HCID 24287Tin tetrachloride

HCID 65578Oxalyl chloride

HCID 102419632,3-Dimethyl-5-benzylthiophene

HCID 234456633.5-Diethyl-4-methoxybenzoic acid

Product 1

HCID 18430717HCID 18430717, compoundYield 99%

Procedure

The title compound was prepared according to the procedure in Example 1, step 4, using 3,5-diethyl-4-methoxybenzoic acid (9.45 g, 45.5 mmol), oxalyl chloride (4.35 mL, 50.0 mmol), N,N-DMF (2 drops), tin(IV) chloride (5.85 mL, 50.0 mmol) and 2-benzyl-4,5-dimethylthiophene (11.0 g, 54.6 mmol) to give 17.67 g (99%) of the title compound. 1H NMR δ 1.13 (t, 6 H), 1.83 (s, 3 H), 2.27 (s, 3 H), 2.64 (q, 4 H), 3.73 (s, 3 H), 3.85 (s, 2 H), 7.04 (d, 2 H), 7.12-7.24 (m, 3 H), 7.43 (s, 2 H).

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-fd0d056567814b0eb775becda7bffd32
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06121271

Reaction notes

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