Ethanol → HCID 53825677, compound

HRID 1583815Notes

Reaction equation

HRID 1583815 reaction equation
[CH2:1](Br)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Na].[SH:12][C@@H:13]1[O:21][C@H:20]([CH2:22][OH:23])[C@@H:18]([OH:19])[C@H:16]([OH:17])[C@@H:14]1[OH:15].[CH2:24]([OH:26])[CH3:25]>O>[C:24]([O:15][C@H:14]1[C@@H:16]([O:17][C:14](=[O:15])[CH3:13])[C@H:18]([O:19][C:16](=[O:17])[CH3:18])[C@@H:20]([CH2:22][O:23][C:20](=[O:21])[CH3:22])[O:21][C@H:13]1[S:12][CH2:1][CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 702EthanolHCID 98116BromomethylstyreneHCID 86740513HCID 86740513, compound

Product 1

HCID 53825677HCID 53825677, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of cinnamyl bromide (0.45 g) in ethanol (4 ml) is added to a solution of 1-thio-β-D-mannopyranose sodium salt (0.5 g) in water (6 ml). After 20 minutes at room temperature, the solution is evaporated in vacuo to a crystalline mass. Pyridine (10 ml) and acetic anhydride (10 ml) are added, and the solution is kept at room temperature for 3 hours and poured into ice-water. The solid is collected and washed with cold water. Recrystallization from methanol affords 4 (0.93 g, 85%); m.p. 113°-114° C.; [α]D27 -130±1.0° (C 1.0, chloroform).

Workup

  1. customthe solution is evaporated in vacuo to a crystalline mass
  2. additionPyridine (10 ml) and acetic anhydride (10 ml) are added
  3. waitthe solution is kept at room temperature for 3 hours
  4. additionpoured into ice-water
  5. customThe solid is collected
  6. washwashed with cold water
  7. customRecrystallization from methanol

Sources & evidence

ORD record
ord-1e8a86efe7ff460c9a090cae5ed12de5
Source dataset
uspto-grants-1985_11
Patent number
US04554349

Reaction notes

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