Dimethyl Sulfoxide → 3-(R)-methyl-5-(t-butyldimethylsilyloxy)-1-pentanal

HRID 35721ノート

反応式

HRID 35721 の反応式
C(Cl)(=O)C(Cl)=O.C(Cl)Cl.CS(C)=O.[CH3:14][C@H:15]([CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:16][CH2:17][OH:18]>C(N(CC)CC)C>[CH3:14][C@H:15]([CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:26])([CH3:28])[CH3:27])([CH3:24])[CH3:23])[CH2:16][CH:17]=[O:18]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 6344Dichloromethane2 回HCID 65578Oxalyl chlorideHCID 100826933-(S)-methyl-5-(t-butyldimethylsilyloxy)-1-pentanol

生成物 1

HCID 104438663-(R)-methyl-5-(t-butyldimethylsilyloxy)-1-pentanal

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

To 56.3 g. of oxalyl chloride in 300 ml. of dry methylene chloride cooled to -60° C. and under a nitrogen atmosphere was added dropwise 74.81 g. of dimethylsulfoxide in 100 ml. of dry methylene chloride. After 15 minutes 92.0 g. of 3-(S)-methyl-5-(t-butyldimethylsilyloxy)-1-pentanol in 250 ml. of the same solvent was added dropwise. After 30 minutes 206.1 g. of triethylamine was added to -60° C. followed by the removal of the cooling bath. The reaction was stirred at room temperature for 1.5 hours, and was then poured into water and extracted with methylene chloride. The extracts were washed with 2.5% hydrochloric, a saturated sodium bicarbonate solution, water and a brine solution, and then dried over magnesium sulfate. The solvent was removed and the residue dissolved in ether and rewashed and dried as before. Removal of the ether gave 90.9 g. of the desired product.

後処理

  1. additionwas added dropwise 74.81 g
  2. additionof the same solvent was added dropwise
  3. waitAfter 30 minutes 206.1 g
  4. customfollowed by the removal of the cooling bath
  5. additionwas then poured into water
  6. extractionextracted with methylene chloride
  7. washThe extracts were washed with 2.5% hydrochloric
  8. dry with materiala saturated sodium bicarbonate solution, water and a brine solution, and then dried over magnesium sulfate
  9. customThe solvent was removed
  10. dissolutionthe residue dissolved in ether
  11. customdried as before
  12. customRemoval of the ether
  13. customgave 90.9 g

出典と根拠

ORDレコード
ord-154a74fe8a0c4d619de5a5dbe7a96915
出典データセット
uspto-grants-1988_08
特許番号
US04767743

反応ノート

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