Carbon Dioxide → HCID 15481240, compound

HRID 1873130Notes

Reaction equation

HRID 1873130 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[CH2:6][C:7]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[CH:8]=1.[C:19](Cl)(=O)[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1.[Sn].C(=O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:16]2[C:5](=[CH:6][C:7]3[S:11][C:10]4[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=4[C:8]=3[C:19]=2[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH:4]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 7477p-Anisoyl chlorideHCID 5352426Tin atomHCID 15481279HCID 15481279, compound

Product 1

HCID 15481240HCID 15481240, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (-78° C.) solution of 2-(3-methoxybenzyl)-benzo[b]thiophene (2.10 g, 8.26 mmol) and p-anisoyl chloride (1.48 g, 8.67 mmol) in anhydrous methylene chloride (31 mL) was added tin IV chloride (2.90 mL, 24.8 mmol, 3 eq) dropwise over a period of 24 minutes. After stirring overnight in the warming dry ice bath and at ambient temperature for 7 hours the reaction mixture was poured onto water (175 mL) and the organics were extracted with diethyl ether (2×300 mL). The extracts were combined, and washed with brine. Silica gel was added and the solvent was removed. The adsorbate was flash chromatographed (97/3 petroleum ehter/ethyl acetate) to give the title compound as a white solid (1.92 g, 63%): mp 158-159° C.; MS (+FAB): [M+] 370; Anal. Calc. for C24H18O2S: C, 77.81, H, 4.90, N, 0.00. Found: C, 78.00, H, 4.76, N, 0.03.

Workup

  1. additionwas poured onto water (175 mL)
  2. extractionthe organics were extracted with diethyl ether (2×300 mL)
  3. washwashed with brine
  4. additionSilica gel was added
  5. customthe solvent was removed
  6. customchromatographed (97/3 petroleum ehter/ethyl acetate)

Sources & evidence

ORD record
ord-a18afcd929e5455fa655a1799be46230
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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