Water → HCID 66959155, compound

HRID 1367747Notes

Reaction equation

HRID 1367747 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:30][CH3:31])=[CH:11][C:12]2[CH:13]3[CH:21]([CH2:22][CH2:23][C:24]=2[CH:25]=1)[CH:20]1[C:16]([CH3:29])([C:17](=[CH:26][CH2:27][OH:28])[CH2:18][CH2:19]1)[CH2:15][CH2:14]3)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:34]I.O>C1COCC1>[CH2:1]([O:8][C:9]1[C:10]([CH2:30][CH3:31])=[CH:11][C:12]2[CH:13]3[CH:21]([CH2:22][CH2:23][C:24]=2[CH:25]=1)[CH:20]1[C:16]([CH3:29])([C:17](=[CH:26][CH2:27][O:28][CH3:34])[CH2:18][CH2:19]1)[CH2:15][CH2:14]3)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66960227HCID 66960227, compound

Product 1

HCID 66959155HCID 66959155, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(3-Benzyloxy-2-ethyl-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-ylidene)-ethanol (0.62 g, 1.5 mmol) in 10 ml dry THF was cooled to 0° C. under nitrogen. NaH (0.08 g, 2 mmol of NaH 60% dispersion in mineral oil) was added portion wise and the solution stirred for 30 minutes before CH3I (0.19 ml, 3 mmol) was added dropwise. The solution was then allowed to warm to room temperature and stirred for 18 hours. After addition of water (20 ml) the organics were extracted with ethylacetate. The organic layer was washed with water, brine, dried over MgSO4 and the solvents were evaporated under vacuum. The crude oil was purified by chromatography (hexane/ethylacetate 20/1) to give 3-benzyloxy-2-ethyl-17-(2-methoxy-ethylidene)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene, 0.59 g (91%), as a colourless oil; 1H NMR (CDCl3, 270 MHz): 0.84 (s, 3H, CH3), 1.24 (t, J=7.4 Hz, 3H, CH3), 1.26-1.66 (m, 6H), 1.82-2.02 (m, 3H), 2.20-2.51 (m, 3H), 2.70 (q, J=7.4 Hz, 2H, CH2), 2.87 (m, 2H, H6), 3.36 (s, 3H, CH3O), 3.94 (m, 2H, CH2OMe), 5.06 (s, 2H, CH2Ph), 5.27 (m, 1H, CHCH2OH), 6.66 (s, 1H, ArH), 7.15 (s, 1H, ArH), 7.31-7.48 (m, 5H, Ph).

Workup

  1. additionwas added dropwise
  2. extractionorganics were extracted with ethylacetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over MgSO4
  5. customthe solvents were evaporated under vacuum
  6. customThe crude oil was purified by chromatography (hexane/ethylacetate 20/1)

Sources & evidence

ORD record
ord-1b0290ccc9aa480da5b11ebeabe45571
Source dataset
uspto-grants-2011_02
Patent number
US07893284B2

Reaction notes

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