Sodium ethoxide → HCID 87903859, compound

HRID 1825302Notes

Reaction equation

HRID 1825302 reaction equation
[CH3:1][C:2](=[CH:8][CH:9]=[CH:10][C:11]([CH3:20])=[CH:12][CH:13]=[CH:14][CH:15]=[C:16]([CH3:19])[CH:17]=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl-].[CH3:22][C:23]1([CH3:52])[CH2:28][O:27][CH:26]([C:29]([CH3:51])=[CH:30][CH2:31][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[O:25][CH2:24]1.[O-]CC.[Na+]>ClCCl.[Cl-].[Na+].O>[CH3:22][C:23]1([CH3:52])[CH2:24][O:25][CH:26]([C:29]([CH3:51])=[CH:30][CH:31]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=[CH:13][CH:12]=[C:11]([CH3:20])[CH:10]=[CH:9][CH:8]=[C:2]([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[O:27][CH2:28]1

Participants

6

Reactant 3

HCID 2723922Sodium ethoxideHCID 72394690HCID 72394690, compoundHCID 73867066HCID 73867066, compound

Product 1

HCID 87903859HCID 87903859, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

13.7 g (50 mmol) of the product from step b) were dissolved in 125 ml of dichloromethane. 25.7 g (55 mmol) of 3-(5,5-dimethyl-1,3-dioxan-2-yl)but-2-enyltriphenylphosphonium chloride were added. At 0° C., 20.4 g of a 20% strength ethanolic solution of sodium ethoxide (60 mmol) were added over the course of 1 hour. The mixture was stirred at 0° C. for 1 hour and then 50 ml of semiconcentrated brine were added. The organic phase was separated off, washed once with 50 ml of semiconcentrated brine, dried over sodium sulfate and concentrated in a rotary evaporator at 20° C. down to 20 mbar. The residue (38.2 g) was purified by flash chromatography on silica gel (eluent: cyclohexane/methyl t-butyl ether 4:1). 19.9 g (93.4% of theory) of the title compound were obtained. For characterization, the product was dissolved by heating in 100 ml of ethyl acetate. 50 ml of diisopropyl ether were added to the hot solution and, after cooling to 0° C., the mixture was stirred for 1 hour. The crystals which formed were filtered off, washed with cold ethyl acetate/diisopropyl ether mixture (2:1 vol./vol.) and dried in a stream of nitrogen. Yield: 8.9 g of red crystals. Melting point 157.5 to 158° C. E11 (CHCl3): 2495 (423 nm), 2243 (448 nm).

Workup

  1. customThe organic phase was separated off
  2. washwashed once with 50 ml of semiconcentrated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in a rotary evaporator at 20° C. down to 20 mbar
  5. customThe residue (38.2 g) was purified by flash chromatography on silica gel (eluent: cyclohexane/methyl t-butyl ether 4:1)

Sources & evidence

ORD record
ord-57a92c6578904d6d80cc154051c17614
Source dataset
uspto-grants-2006_05
Patent number
US07045641B2

Reaction notes

Loading…