Sodium Hydroxide → HCID 53646573, compound

HRID 2399341Notes

Reaction equation

HRID 2399341 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]1[O:23][C:22](=[O:24])[CH2:21][C:20]1([OH:29])[C:25]([O:27]C)=[O:26]>CO.O>[C:25]([C@:20]1([OH:29])[C@@H:19]([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:5]2[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:4]=2[Cl:3])[O:23][C:22](=[O:24])[CH2:21]1)([OH:27])=[O:26]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19387361HCID 19387361, compound

Product 1

HCID 53646573HCID 53646573, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Aqueous NaOH (1M, 4 ml, 4.0 mmol) was added dropwise to a stirred solution of ±(4R*,5R*,) 5-[8-(2,4-dichlorophenyl)-octyl]-4-hydroxy-4 -methoxycarbonyltetrahydrofuran-2-one (198 mg, 0.474 mmol) in methanol (4 ml) at 0° C. The solution was stirred at room temperature for 24 h, diluted with water, and washed with ether. The aqueous phase was acidified (aqueous HCl), and extracted with ether. The extracts were washed with water, saturated aqueous NaCl, and dried (MgSO4). The solvent was removed under vacuum. The crude diacid was stirred with silica gel (3 g), impregnated with 2M aqueous H2SO4 (0.15 ml), in ether for 1 h. The mixture was filtered, and the solvent removed from the filtrate under vacuum to give the title compound (107 mg), (δ 200 MHz, CDCl3) 7.34-7.10 (3H, m), 4.66 (1H, dd), 3.25 (1H, d), 2.77 (1H, d), 2.67 (2H, t), 1.95-1.20 (14H, m), contaminated with a small amount of ±(E) (4R*,5R*) 4-carboxy-5-[8-(2,4-dichlorophenyl)-7-octenyl]-4-hydroxytetrahydrofuran-2-one.

Workup

  1. washwashed with ether
  2. extractionextracted with ether
  3. washThe extracts were washed with water, saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed under vacuum
  6. stirringThe crude diacid was stirred with silica gel (3 g)
  7. waitimpregnated with 2M aqueous H2SO4 (0.15 ml), in ether for 1 h
  8. filtrationThe mixture was filtered
  9. customthe solvent removed from the filtrate under vacuum

Sources & evidence

ORD record
ord-fd4ab070d7aa444981be028bebff26d3
Source dataset
uspto-grants-1995_09
Patent number
US05447954

Reaction notes

Loading…