Sodium Sulfate → (R)-(+)-4-tert. butoxy-3-methyl-1-butanol

HRID 2072354ノート

反応式

HRID 2072354 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][CH2:12][C@H:13]([CH3:18])[CH2:14][C:15](O)=[O:16])([CH3:10])([CH3:9])[CH3:8].[O-]S([O-])(=O)=O.[Na+].[Na+]>CCOCC>[C:7]([O:11][CH2:12][C@H:13]([CH3:18])[CH2:14][CH2:15][OH:16])([CH3:9])([CH3:10])[CH3:8]

参加物

5

反応物 3

HCID 24436Sodium SulfateHCID 14658374(R)-(+)-4-tert. butoxy-3-methylbutyric acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 86735110(R)-(+)-4-tert. butoxy-3-methyl-1-butanol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

A slurry of 1.51 g. (0.0398 mole) of lithium aluminum hydride in 50 ml. of ether was stirred and cooled while a solution of 3.45 g. (0.0198 mole) of (R)-(+)-4-tert. butoxy-3-methylbutyric acid in 50 ml. of ether was added dropwise. After the addition was complete , the reaction mixture was stirred room temperature for 2 hours then cooled to 0° C. and cautiously decomposed 5.4 ml. saturated aqueous Na2SO4 solution. After stirring at room temperature for 18 hours, the mixture was filtered and the filtrate was concentrated under reduced pressure. The crude product (3.05 g.) was chromatographed on 10 of silica gel. Elution with 2:1 parts by volume, 1:1 parts by volume and 1:2 parts by volume hexane-ether followed by evaporative distillation gave 2.68 (85%) of the (R)-(+)-4-tert. butoxy-3-methyl-1-butanol as a colorless liquid b.p. 100°-102° C. (bath temperature) (20 mm Hg.); [α]25D + 12.79° (c 2.19, C6H6).

後処理

  1. temperaturecooled while a solution of 3.45 g
  2. additionAfter the addition
  3. temperaturethen cooled to 0° C.
  4. stirringAfter stirring at room temperature for 18 hours
  5. filtrationthe mixture was filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe crude product (3.05 g.) was chromatographed on 10 of silica gel
  8. washElution with 2:1 parts by volume, 1:1 parts by volume and 1:2 parts by volume hexane-ether
  9. distillationfollowed by evaporative distillation

出典と根拠

ORDレコード
ord-c351e3c286a34cc69ed1fdeb9d8c9559
出典データセット
uspto-grants-1977_09
特許番号
US04051153

反応ノート

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