Oxalyl chloride → HCID 15895036, compound

HRID 1280927Notes

Reaction equation

HRID 1280927 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.[Br:23][C:24]1[CH:37]=[CH:36][C:27]([CH2:28][C:29]2[S:30][C:31]([CH3:35])=[C:32]([CH3:34])[CH:33]=2)=[CH:26][CH:25]=1>CN(C)C=O>[Br:23][C:24]1[CH:37]=[CH:36][C:27]([CH2:28][C:29]2[S:30][C:31]([CH3:35])=[C:32]([CH3:34])[C:33]=2[C:9]([C:8]2[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:6]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:7]=2)=[O:11])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 158950343-Cyclopentyl-p-anisic acidHCID 15895035HCID 15895035, compound

Product 1

HCID 15895036HCID 15895036, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

The title compound was prepared according to the procedure in Example 5, step 2 using 3-cyclopentyl-p-anisic acid (3.50 g, 15.9 mmol, RN-59216-82-9), oxalyl chloride (1.52 mL, 17.5 mmol), N,N-dimethylformamide (2 drops) tin(IV) chloride (2.04 mL, 17.5 mmol) and 2-(4-bromobenzyl)4,5-dimethylthiophene (4.46 g, 15.9 mmol). Purification on silica gel eluting 5% EtOAc/pet. ether gave 4.05 g (53%) of the title compound as yellow oil. (DMSO-d6) δ 1.43-1.47 (m, 2H), 1.61-1.75 (m, 4H), 1.81 (s, 3H), 1.91-1.99 (m, 2H), 2.28 (s, 3H), 3.24 (quintet, 1H), 3.84 (s, 2H), 3.88 (s, 3H), 7.02 (d, 2H), 7.06 (d, 1H), 7.40 (d, 2H), 7.52 (dd, 1H), 7.57 (d, 1H).

Workup

  1. customThe title compound was prepared
  2. customPurification on silica gel eluting 5% EtOAc/pet. ether

Sources & evidence

ORD record
ord-d1e7835b0b304f62ace01c85118eb4eb
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

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