Water → HCID 24748418, compound

HRID 1613113Notes

Reaction equation

HRID 1613113 reaction equation
[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12](/[C:15](/[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:16](/Cl)\[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:13][CH:14]=1)[CH2:4][CH3:5].C([Li])(C)(C)C.[CH2:35]1[O:37][CH2:36]1.O>O1CCCC1>[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12](/[C:15](/[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:16](\[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)/[CH2:35][CH2:36][OH:37])=[CH:13][CH:14]=1)[CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6354Ethylene OxideHCID 1548953EnclomipheneHCID 178418306HCID 178418306, compound

Product 1

HCID 24748418HCID 24748418, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Clomiphene (6.06 g, 14.9 mmol) was dissolved in tetrahydrofuran (100 ml) and cooled to -40° C. t-Butyl lithium (1M in pentane, 24 mmol) was added slowly. After 5 minutes, ethylene oxide (14.6 ml, 290 mmol) was added, and the reaction mixture was stirred for 6 hours, poured into water and extracted with ether. The ether layer was evaporated and chromatographed on a silica gel column using 1:1:0.1 ether/petroleum ether/triethylamine as eluant to yield trans product (1.96 g, 27.1%, oil): and cis product (1.56 g, 21.5%, oil): Assignment of 1HNMR for aliphatic protons are presented in Table 1.

Workup

  1. additionwas added slowly
  2. extractionextracted with ether
  3. customThe ether layer was evaporated
  4. customchromatographed on a silica gel column
  5. customto yield trans product (1.96 g, 27.1%, oil)

Sources & evidence

ORD record
ord-34927f6891b2430cabbc733ceb8c0162
Source dataset
uspto-grants-1993_03
Patent number
US05192525

Reaction notes

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