Sodium hydride → HCID 14986330, compound

HRID 1613055Notes

Reaction equation

HRID 1613055 reaction equation
[H-].[Na+].[C:3]1([CH2:9][O:10][C:11](=[O:23])[C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH2:19][CH2:20][CH3:21])[C:13]=2[OH:22])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([O:37][C:38](=[O:40])[CH3:39])[C:32]=1[O:41][C:42](=[O:44])[CH3:43]>CN(C)C=O>[C:3]1([CH2:9][O:10][C:11](=[O:23])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([O:37][C:38](=[O:40])[CH3:39])[C:32]=3[O:41][C:42](=[O:44])[CH3:43])=[C:14]([CH2:19][CH2:20][CH3:21])[C:13]=2[OH:22])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 14986287HCID 14986287, compoundHCID 14986292HCID 14986292, compound

Product 1

HCID 14986330HCID 14986330, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 0.14 g (3.5 mmol, 60% on oil) of sodium hydride in 10 mL of anhydrous dimethylformamide stirred at room temperature was added 0.88 g (3.1 mmol) of 2,4-dihydroxy-3-propylbenzoic acid phenylmethyl ester. The reaction mixture was stirred for 2 hours and then 1.09 g (3.1 mmol) of 1-(6-bromohexyl)-2,3-bis(acetyloxy)benzene in 10 mL of dimethylformamide was added dropwise. Stirring at 50° was continued for 16 hours and then the solvent was removed on the oil pump. The crude product was purified by HPLC using 25% ethyl acetate-hexane to give 0.55 g (28% yield) of 4-[6-[2,3-bis(acetyloxy)phenyl]hexyloxy]-2-hydroxy-3-propylbenzoic acid phenylmethyl ester as an oil.

Workup

  1. stirringThe reaction mixture was stirred for 2 hours
  2. stirringStirring at 50°
  3. customthe solvent was removed on the oil pump
  4. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-e5bb435a87774a5b95e105adde117276
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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