Epichlorohydrin → HCID 86622515, compound

HRID 2261459Notes

Reaction equation

HRID 2261459 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])=[C:4]([O:24][CH3:25])[CH:3]=1.[CH2:26]([CH:28]1[O:30][CH2:29]1)Cl>C(O)(C)C.[OH-].[Na+].C(OCC)C>[CH3:25][O:24][C:4]1[CH:3]=[C:2]([O:1][CH2:26][CH:28]2[CH2:29][O:30]2)[CH:7]=[CH:6][C:5]=1[CH2:8][CH2:9][C:10]([C:12]1[S:19][C:18]([CH3:20])=[C:17]2[C:13]=1[CH2:14][C@H:15]1[C:21]([CH3:22])([CH3:23])[C@H:16]12)=[O:11]

Participants

6

Reactant 2

HCID 7835EpichlorohydrinHCID 59593527HCID 59593527, compound2×

Product 1

HCID 86622515HCID 86622515, compoundYield 66.2%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-(4-hydroxy-2-methoxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (600 mg, 1.68 mmol, Intermediate 20) in isopropanol (10 mL) and 3 N aq. NaOH (6 mL) is treated with epichlorohydrine (631 mg, 5.05 mmol). The reaction mixture is stirred at rt for 9 h before it is diluted with diethyl ether (150 mL) and washed with sat. aq. NaHCO3 followed by water. The organic layer is dried over MgSO4 and evaporated. The crude product is purified by CC on silica gel eluting with heptane:EA 4:1 to give 3-(2-methoxy-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 (459 mg) as an almost colourless oil; LC-MS: tR=1.13 min, [M+1]+=413.28.

Workup

  1. washwashed with sat. aq. NaHCO3
  2. dry with materialThe organic layer is dried over MgSO4
  3. customevaporated
  4. customThe crude product is purified by CC on silica gel eluting with heptane:EA 4:1

Sources & evidence

ORD record
ord-b5d45565a4ee479f94cb9a79c71e0528
Source dataset
uspto-grants-2010_12
Patent number
US07846964B2

Reaction notes

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