1,2-Dimethoxyethane → HCID 18609920, compound

HRID 1722499Notes

Reaction equation

HRID 1722499 reaction equation
C([O:3][C:4]([C@H:6]1[C@H:10]([C:11]([O:13]CC)=[O:12])[O:9][C:8]([CH:28]([Br:30])[CH3:29])([C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([O:26][CH3:27])[CH:22]=3)[CH:17]=2)[O:7]1)=[O:5])C.[OH-].[Na+].C(COC)OC>O>[Br:30][CH:28]([C:8]1([C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([O:26][CH3:27])[CH:22]=3)[CH:17]=2)[O:7][C@@H:6]([C:4]([OH:5])=[O:3])[C@H:10]([C:11]([OH:13])=[O:12])[O:9]1)[CH3:29]

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 14798Sodium HydroxideHCID 54053096HCID 54053096, compound

Product 1

HCID 18609920HCID 18609920, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of the two diastereoisomers of 2-(1-bromoethyl)-2(6-methoxy-2-naphthyl)-1,3-dioxolane-4(R),5(R)-dicarboxylic acid diethyl ester 3 and 4 (prepared in a similar manner as described in Example 1) (21.18 g, 0.044 mol, ratio 3:4=1:1), sodium hydroxide (3.52 g, 0.088 mol), dimethoxyethane (35 ml) and of water (35 ml) was kept, under stirring, at room temperature for 2 hours. The reaction mixture was diluted with water and extracted with diethylether. The aqueous phase was acidified with concentrated hydrochloric acid to pH 1 and extracted with diethylether. The organic phase was washed with water and dried over sodium sulphate. Evaporation of the solvent under reduced pressure gave the two diastereoisomers of 2-(1-bromoethyl)-2-(6-methoxy-2-naphthyl)-1,3-dioxolane-4(R),5(R)-dicarboxylic acid 5 and 6 (16 g, 0.0367 mol; yield 85.5%) in ratio 5:6=1:1 (determined by 1H-NMR 200 MHz).

Workup

  1. customprepared in a similar manner
  2. extractionextracted with diethylether
  3. extractionextracted with diethylether
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulphate
  6. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-51dfe8464a5b45b19352adbf643f747b
Source dataset
uspto-grants-1989_08
Patent number
US04855464

Reaction notes

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