Epichlorohydrin → HCID 86622509, compound

HRID 2261447Notes

Reaction equation

HRID 2261447 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([C:13]2[S:20][C:19]([CH3:21])=[C:18]3[C:14]=2[CH2:15][C@H:16]2[C:22]([CH3:24])([CH3:23])[C@H:17]23)=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].[CH2:25]([CH:27]1[O:29][CH2:28]1)Cl>C(O)(C)C.[OH-].[Na+].C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([C:13]2[S:20][C:19]([CH3:21])=[C:18]3[C:14]=2[CH2:15][C@H:16]2[C:22]([CH3:24])([CH3:23])[C@H:17]23)=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][CH2:25][CH:27]1[CH2:28][O:29]1

Participants

6

Reactant 2

HCID 7835EpichlorohydrinHCID 59593552HCID 59593552, compound2×

Product 1

HCID 86622509HCID 86622509, compoundYield 24.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 3776IsopropanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-(3-chloro-4-hydroxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (139 mg, 0.385 mmol, Intermediate 6) in isopropanol (4 mL) and 3 N aq. NaOH (1.7 mL) is treated with epichlorohydrine (110 mg, 1.16 mmol). The reaction mixture is stirred at rt for 18 h. The mixture is diluted with acetic acid (0.3 mL) and the solvent is removed under reduced pressure. The residue is purified by prep. HPLC (Waters Xterra MS18, 75×30 mm ID, 10 μm, 10 to 95% acetonitrile in water containing 0.5% formic acid) to give 3-(3-chloro-4-oxiranylmethoxy-phenyl)-1-((1aS,5aR)1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (39 mg) as a pale yellow oil; LC-MS: tR=1.15 min, [M+1]+=417.21.

Workup

  1. customthe solvent is removed under reduced pressure
  2. customThe residue is purified by prep

Sources & evidence

ORD record
ord-901271cc96124d8fbc03657f377c7db1
Source dataset
uspto-grants-2010_12
Patent number
US07846964B2

Reaction notes

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