Water → HCID 57827693, compound

HRID 1842267Notes

Reaction equation

HRID 1842267 reaction equation
O.[Cl-].[NH4+].[Br:4][C:5]1[CH:6]=[C:7]([C:11]23[O:17][CH:16]2[CH2:15][O:14][CH2:13][CH2:12]3)[CH:8]=[CH:9][CH:10]=1.[N-:18]=[N+:19]=[N-:20].[Na+]>CO>[N:18]([C@@:11]1([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([Br:4])[CH:6]=2)[CH2:12][CH2:13][O:14][CH2:15][C@@H:16]1[OH:17])=[N+:19]=[N-:20]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 578277501,5:2,3-Dianhydro-3-C-(3-bromophenyl)-4-deoxypentitol

Product 1

HCID 57827693HCID 57827693, compoundYield 108.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Water (88 mL) and ammonium chloride (11.7 g) were added to a solution of (±)-6-(3-bromophenyl)-3,7-dioxa-bicyclo[4.1.0]heptane (17.5 g) in methanol (700 mL), followed by stirring at room temperature. Then, sodium azide (32.1 g) was added, followed by stirring at 80° C. for eight hours. After returning to room temperature, the excess of methanol was evaporated under reduced pressure. The residual aqueous layer was extracted with chloroform three times, and the organic layers were dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (22.1 g).

Workup

  1. stirringby stirring at 80° C. for eight hours
  2. customAfter returning to room temperature
  3. customthe excess of methanol was evaporated under reduced pressure
  4. extractionThe residual aqueous layer was extracted with chloroform three times
  5. dry with materialthe organic layers were dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-41177962b844444a86729e1481f6a3a9
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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