Epichlorohydrin → HCID 86622508, compound

HRID 2261446Notes

Reaction equation

HRID 2261446 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([C:12]2[S:19][C:18]([CH3:20])=[C:17]3[C:13]=2[CH2:14][C@H:15]2[C:21]([CH3:23])([CH3:22])[C@H:16]23)=[O:11])=[CH:4][C:3]=1[CH3:24].[CH2:25]([CH:27]1[O:29][CH2:28]1)Cl>C(O)(C)C.[OH-].[Na+].C(O)(=O)C>[CH3:24][C:3]1[CH:4]=[C:5]([CH2:8][CH2:9][C:10]([C:12]2[S:19][C:18]([CH3:20])=[C:17]3[C:13]=2[CH2:14][C@H:15]2[C:21]([CH3:22])([CH3:23])[C@H:16]23)=[O:11])[CH:6]=[CH:7][C:2]=1[O:1][CH2:25][CH:27]1[CH2:28][O:29]1

Participants

6

Reactant 2

HCID 7835EpichlorohydrinHCID 59593547HCID 59593547, compound2×

Product 1

HCID 86622508HCID 86622508, compoundYield 32.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 3776IsopropanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-(4-hydroxy-3-methyl-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (179 mg, 0.525 mmol, Intermediate 4) in isopropanol (10 mL) and 3 N aq. NaOH (4 mL) is treated with epichlorohydrine (197 mg, 1.58 mmol). The reaction mixture is stirred at 70 for 1.5 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-methyl-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 (68 mg) as a pale brown oil; LC-MS: tR=1.15 min, [M+1]+=397.27.

Workup

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

Sources & evidence

ORD record
ord-c5cffb7092de4a32812a2364013d3872
Source dataset
uspto-grants-2010_12
Patent number
US07846964B2

Reaction notes

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