Methanol → HCID 70360554, compound

HRID 1073453Notes

Reaction equation

HRID 1073453 reaction equation
[C:1]1([C:7]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:8][CH2:9][C@@H:10]2[O:16][C@H:15]([CH2:17][O:18][C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@@H:13]([OH:14])[C@@H:11]2[OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:52](Br)[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.CO>CN(C)C=O>[C:53]1([CH2:52][O:14][C@H:13]2[C@H:11]([O:12][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C@@H:10]([CH2:9][O:8][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[O:16][C@H:15]2[CH2:17][O:18][C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 70360336HCID 70360336, compound

Product 1

HCID 70360554HCID 70360554, compoundYield 165.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 800 mg of 2,5-anhydro-1,6-bis-O-(triphenylmethyl)-D-glucitol in 16 ml of dry dimethylformamide was treated with 240 mg of freshly washed sodium hydride. The mixture was stirred 1.5 hours, then 1.30 g of benzyl bromide was added and stirring continued for 2.5 days. Methanol was added, the solvents removed in vacuo and the residue taken up in chloroform/water. The organic layer was washed with water and brine, then dried and evaporated, giving a yellow oil which was flash chromatographed, eluting with hexane:ethyl acetate (12:1), giving 847 mg of the desired compound.

Workup

  1. stirringstirring
  2. waitcontinued for 2.5 days
  3. customthe solvents removed in vacuo
  4. washThe organic layer was washed with water and brine
  5. customdried
  6. customevaporated
  7. customgiving a yellow oil which
  8. customchromatographed
  9. washeluting with hexane:ethyl acetate (12:1)

Sources & evidence

ORD record
ord-e80a3f98a7464b648780a6e63fe61cb7
Source dataset
uspto-grants-1990_11
Patent number
US04968790

Reaction notes

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