Sodium Hydroxide → HCID 85809393, compound

HRID 2414999Notes

Reaction equation

HRID 2414999 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH2:19][OH:20])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[C:23]([O:27][C:28](=[O:31])[CH2:29]Br)([CH3:26])([CH3:25])[CH3:24]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:23]([O:27][C:28](=[O:31])[CH2:29][O:20][CH2:19][CH:10]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 43908021,2-di-O-benzyl-glycerol

Product 1

HCID 85809393HCID 85809393, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

100 g (376.2 mmol) of 1,2-di-O-benzyl-glycerol [produced according to Chem. Phys. Lipids (1987), 43(2), 113-277] and 5 g of tetrabutylammonium hydrogen sulfate are dissolved in a mixture that consists of 400 ml of toluene and 200 ml of 50% aqueous sodium hydroxide solution. At 0° C., 78 g (400 mmol) of 2-bromoacetic acid-t butyl ester is added in drops over 30 minutes, and then it is stirred for 3 hours at 0° C. The organic phase is separated, dried on magnesium sulfate and evaporated to the dry state in a vacuum. The residue is chromatographed on silica gel (mobile solvent: n-hexane/acetone=20:1).

Workup

  1. customThe organic phase is separated
  2. customdried on magnesium sulfate
  3. customevaporated to the dry state in a vacuum
  4. customThe residue is chromatographed on silica gel (mobile solvent: n-hexane/acetone=20:1)

Sources & evidence

ORD record
ord-ad49a539b6404895adaada7e54f5e627
Source dataset
uspto-grants-2004_11
Patent number
US06818203B2

Reaction notes

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