Dimethyl Sulfoxide → HCID 178418459、化合物

HRID 881

反応式

HRID 881 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Si:11]([O:18][C@H:19]1[CH2:24][CH2:23][C@H:22](/[CH:25]=[C:26](\[CH3:29])/[CH2:27][OH:28])[CH2:21][CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[Si:11]([O:18][C@H:19]1[CH2:20][CH2:21][C@H:22](/[CH:25]=[C:26](\[CH3:29])/[CH:27]=[O:28])[CH2:23][CH2:24]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 178418307HCID 178418307、化合物

生成物 1

HCID 178418459HCID 178418459、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a -78° C. solution of oxalyl chloride (105 μL, 1.2 mmol) in 1.0 mL of methylene chloride was added dimethylsulfoxide (170 μL, 2.4 mmol). The resulting solution was stirred for 5 min and then 170 mg (0.6 mmol) of the alcohol 135 was added in 1.0 mL of methylene chloride. The reaction mixture was stirred at -78° C. for 45 min at which time 500 μL (3.6 mmol) of triethylamine was added and the solution was allowed to warm to ambient temperature. The reaction was quenched with 1.0N HCl and the aqueous layer was extracted with three portions of methylene chloride. The combined organic extracts were dried over MgSO4 and evaporated to dryness to give the crude aldehyde 136 which was used directly in the next reaction. 1H NMR consistent with structure.

後処理

  1. additionwas added
  2. customThe reaction was quenched with 1.0N HCl
  3. extractionthe aqueous layer was extracted with three portions of methylene chloride
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-2a5760aaa3d049789dc0038907f707bb
出典データセット
uspto-grants-1998_03
特許番号
US05723459

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