Epichlorohydrin → HCID 86622514, compound

HRID 2261458Notes

Reaction equation

HRID 2261458 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]([C:13]1[S:20][C:19]([CH3:21])=[C:18]2[C:14]=1[CH2:15][C@H:16]1[C:22]([CH3:24])([CH3:23])[C@H:17]12)=[O:12].[CH2:25]([CH:27]1[O:29][CH2:28]1)Cl>C(O)(C)C.[OH-].[Na+].C(OCC)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:25][CH:27]2[CH2:28][O:29]2)[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]([C:13]1[S:20][C:19]([CH3:21])=[C:18]2[C:14]=1[CH2:15][C@H:16]1[C:22]([CH3:24])([CH3:23])[C@H:17]12)=[O:12]

Participants

6

Reactant 2

HCID 7835Epichlorohydrin2×HCID 59593548HCID 59593548, compound2×

Product 1

HCID 86622514HCID 86622514, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-(2-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 (400 mg, 1.11 mmol, Intermediate 18) in isopropanol (10 mL) and 3 N aq. NaOH (6 mL) is treated with epichlorohydrine (554 mg, 4.43 mmol). The dark red reaction mixture is stirred at rt for 6 h before another portion of epichlorohydrine (554 mg, 4.43 mmol) is added. Stirring is continued for 18 h. The mixture 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 7:3 to give 3-(2-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 (222 mg) as a pale yellow oil; LC-MS: tR=1.16 min, [M+1]+=417.20.

Workup

  1. customThe dark red reaction mixture
  2. additionis added
  3. washwashed with sat. aq. NaHCO3
  4. dry with materialThe organic layer is dried over MgSO4
  5. customevaporated
  6. customThe crude product is purified by CC on silica gel eluting with heptane:EA 7:3

Sources & evidence

ORD record
ord-5ff9b90de52745eeb997889ee76ba30d
Source dataset
uspto-grants-2010_12
Patent number
US07846964B2

Reaction notes

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