Water → HCID 6991727、化合物

HRID 2413200ノート

反応式

HRID 2413200 の反応式
[CH3:1][C:2]1([CH3:11])[O:6][C@H:5]([CH2:7][OH:8])[C@@H:4]([CH2:9][OH:10])[O:3]1.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>C1COCC1>[C:15]1([CH2:14][O:8][CH2:7][C@@H:5]2[C@@H:4]([CH2:9][O:10][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:3][C:2]([CH3:11])([CH3:1])[O:6]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

6

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 785244(-)-2,3-O-Isopropylidene-D-threitol

生成物 1

HCID 6991727HCID 6991727、化合物収率 120.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of (4R-trans)-(-)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol (51 g) in THF (400 ml) was added dropwise to a stirred suspension of sodium hydride (17.5 g of 80% in oil) in THF (200 ml). After 0.75 h, benzyl bromide (116.3 g) was added dropwise and the resulting mixture was stirred for 18 h, and was then heated at reflux for 2 h. After stirring for a further 20 h at 20°, the mixture was cooled in ice, water (10 ml) was added and the mixture was evaporated to dryness. The residue was extracted with ER, and the organic solution was dried and the solvent was evaporated giving a crude product (130 g) which was used without further purification.

後処理

  1. temperaturewas then heated
  2. temperatureat reflux for 2 h
  3. stirringAfter stirring for a further 20 h at 20°
  4. temperaturethe mixture was cooled in ice
  5. customthe mixture was evaporated to dryness
  6. extractionThe residue was extracted with ER
  7. customthe organic solution was dried
  8. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-f58bc6b713b54d53ac066533d4079a27
出典データセット
uspto-grants-1985_01
特許番号
US04496579

反応ノート

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