Dimethyl Sulfoxide → Phenoxymethyl ketone

HRID 1379335

反応式

HRID 1379335 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[O:11]([CH2:18][CH:19]([OH:28])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[O:11]([CH2:18][C:19]([CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:28])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 121401,3-Diphenoxy-2-propanolHCID 65578Oxalyl chloride

生成物 1

HCID 13408090Phenoxymethyl ketone収率 83%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 0.44 ml (6.2 mmol) of dimethylsulfoxide in 25 ml of dichloromethane was cooled under inert atmosphere to -63° C., treated with 2.3 ml (4.6 mmol) of oxalyl chloride (2M in dichloromethane), and stirred for 15 min. A solution of 0.75 g (3.1 mmol) of the resultant compound of Example 4 in 10 ml of dichloromethane was subsequently added, the solution was stirred for 30 min, and 1.73 ml (12.4 mmol) of triethylamine was added. After stirring for an additional 15 min, the solution was quenched with 10% aqueous citric acid, poured into a mixture of 1:1 ether:hexane and 10% citric acid, extracted with ether, washed with aqueous brine, dried over MgSO4, and concentrated to a yellow oil. Purification by flash chromatography using 20% ethyl acetate in hexane gave 0.62 g (83%) of the desired compound as a white, crystalline solid, m.p. 55°-57° C. 1H NMR (CDCl3) δ 4.89 (s, 4H), 6.92 (m, 4H), 7.02 (m, 2H), 7.30 (m, 4H). Mass spectrum (M+NH4)+ =260.

後処理

  1. stirringthe solution was stirred for 30 min
  2. stirringAfter stirring for an additional 15 min
  3. customthe solution was quenched with 10% aqueous citric acid
  4. additionpoured into a mixture of 1:1 ether
  5. extractionhexane and 10% citric acid, extracted with ether
  6. washwashed with aqueous brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated to a yellow oil
  9. customPurification by flash chromatography

出典と根拠

ORDレコード
ord-55be877bbea6405f947a6d82e14aac5b
出典データセット
uspto-grants-1997_09
特許番号
US05670675

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