Water → HCID 6991727, 화합물

HRID 2413200노트

반응식

HRID 2413200 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 6991727HCID 6991727, 화합물수율 120.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f58bc6b713b54d53ac066533d4079a27
출처 데이터셋
uspto-grants-1985_01
특허 번호
US04496579

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