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Dimethyl Sulfoxide → 3-Cyclohexyl-3-formyloxetane

HRID 704155
ノート
印刷プレビュー

反応式

HRID 704155 の反応式
[CH:1]1([C:7]2([CH2:11][OH:12])[CH2:10][O:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.CS(C)=O.C(N(CC)CC)C>ClCCl>[CH:1]1([C:7]2([CH:11]=[O:12])[CH2:8][O:9][CH2:10]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19373305(3-Cyclohexyloxetan-3-yl)methanol

生成物 1

HCID 200755923-Cyclohexyl-3-formyloxetane

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

3-Cyclohexyl-3-hydroxymethyloxetane (7.0 g) was dissolved in dry dichloromethane (20 ml) and added dropwise to a mixture of oxalyl chloride (1.1 eq, 4 ml) in dry dichloromethane (15 ml). At -70° C. a solution of dimethyl sulphoxide (7.15 ml) in dichloromethane (10 ml) was added. After stirring at -70° C. for 30 minutes triethylamine (29 ml) was added over 30 minutes. The reaction mixture was allowed to warm up to room temperature over a period of 3 hours and then quenched in water. Extraction with dichloromethane, followed by washing with dilute hydrochloric acid, saturated sodium bicarbonate solution and brine and drying over magnesium sulphate gave a solution which was evaporated to give 3-cyclohexyl-3-formyloxetane as a colourless oil.

後処理

  1. additionwas added over 30 minutes
  2. customquenched in water
  3. extractionExtraction with dichloromethane
  4. washby washing with dilute hydrochloric acid, saturated sodium bicarbonate solution and brine
  5. dry with materialdrying over magnesium sulphate
  6. customgave a solution which
  7. customwas evaporated

出典と根拠

ORDレコード
ord-e5035303f8c2444db1a1781d07cb5e40
出典データセット
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04985582

反応ノート

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