Ammonium Chloride → HCID 58786166, compound

HRID 1375967Notes

Reaction equation

HRID 1375967 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]([CH3:16])[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15].[CH2:17]([O:24][C@@H:25]1[C@@H:31]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@H:30]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C@@H:29]([CH2:48][O:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[O:28][C:26]1=[O:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Cl-].[NH4+]>C1COCC1.CCCCCC>[CH2:17]([O:24][C@@H:25]1[C@@H:31]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@H:30]([O:40][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C@@H:29]([CH2:48][O:49][CH2:50][C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[O:28][C:26]1([C:7]1[CH:8]=[C:9]([CH3:16])[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[OH:27])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 10907626(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)oxan-2-oneHCID 229962372-Bromo-1-ethoxy-4-methylbenzeneHCID 178418339Butyllithium

Product 1

HCID 58786166HCID 58786166, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A 1.6 M hexane solution of n-butyl lithium (11 ml) was added dropwise to a solution of 3-bromo-4-ethoxytoluene (3.6 g) in THF (50 ml) at −78° C. and the mixture was stirred for 15 minutes. Then, a solution of 2,3,4,6-tetra-O-benzyl-D-(+)-glucono-1,5-lactone (7.6 g) in THF (10 ml) was added dropwise to the reaction mixture and the mixture was stirred for 2.5 hours. Saturated aqueous solution of ammonium chloride was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The resulting precipitates were collected by filtration to obtain 2,3,4,6-tetra-O-benzyl-1-C-(2-ethoxy-5-methylphenyl)-D-glucopyranose (3.53 g).

Workup

  1. stirringthe mixture was stirred for 2.5 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated
  7. customThe resulting precipitates
  8. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-72caac0d58c6492aaca3354c3bb190e9
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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