Oxalyl chloride → 6-Benzyloxy-2-(dimethylamino)benzo[b]thiophen-3-yl 3-Methoxy-4-triisopropylsilyloxyphenyl Ketone

HRID 1387105ノート

反応式

HRID 1387105 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][Si:13]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[C:6](O)=[O:7].C(Cl)(=O)C(Cl)=O.[CH2:29]([O:36][C:37]1[CH:38]=[CH:39][C:40]2[CH:44]=[C:43]([N:45]([CH3:47])[CH3:46])[S:42][C:41]=2[CH:48]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([O-])(O)=O.[Na+]>ClC(Cl)C.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]([C:44]2[C:40]3[CH:39]=[CH:38][C:37]([O:36][CH2:29][C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)=[CH:48][C:41]=3[S:42][C:43]=2[N:45]([CH3:46])[CH3:47])=[O:7])[CH:9]=[CH:10][C:11]=1[O:12][Si:13]([CH:17]([CH3:19])[CH3:18])([CH:20]([CH3:21])[CH3:22])[CH:14]([CH3:15])[CH3:16]

参加物

7

反応物 4

HCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 106129946-Benzyloxy-2-dimethylaminobenzo[b]thiopheneHCID 183185063-Methoxy-4-triisopropylsilyloxybenzoic acid

生成物 1

HCID 183185456-Benzyloxy-2-(dimethylamino)benzo[b]thiophen-3-yl 3-Methoxy-4-triisopropylsilyloxyphenyl Ketone

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 63651,1-Dichloroethane溶媒

実験手順

A slurry of 3-methoxy-4-triisopropylsilyloxybenzoic acid (9.75 g, 30 mmol; Part A) in 300 mL of dichloroethane and 1 drop of DMF was treated with oxalyl chloride (13.1 mL, 150 mmol) and stirred overnight at ambient temperature. The reaction mixture was concentrated in vacuo and suspended in 300 mL of chlorobenzene. 6-Benzyloxy-2-(N,N-dimethylamino)benzo[b]thiophene (8.5 g, 30 mmol) was added, and the resulting mixture was heated at 105° C. for 5 h. After cooling to ambient temperature, the reaction mixture was poured into 500 mL of saturated aqueous NaHCO3 solution. The aqueous layer was extracted with CHCl3 (3×150 mL). The combined organics were dried over K2CO3, filtered and concentrated in vacuo. Purification by flash chromatography (SiO2; gradient of 5% to 10% EtOAc in hexanes) afforded 6.05 g (10.3 mmol; 34%) of the title compound.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. temperaturethe resulting mixture was heated at 105° C. for 5 h
  3. temperatureAfter cooling to ambient temperature
  4. extractionThe aqueous layer was extracted with CHCl3 (3×150 mL)
  5. dry with materialThe combined organics were dried over K2CO3
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography (SiO2; gradient of 5% to 10% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-31436a8b0fbe4678b9e7f8a21b2a5e91
出典データセット
uspto-grants-2001_07
特許番号
US06265575B1

反応ノート

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