Aluminium lithium hydride → HCID 66960227, compound

HRID 1367746Notes

Reaction equation

HRID 1367746 reaction equation
C([O:3][C:4](=O)[CH:5]=[C:6]1[C:22]2([CH3:23])[CH:9]([CH:10]3[CH:19]([CH2:20][CH2:21]2)[C:18]2[CH:17]=[C:16]([CH2:24][CH3:25])[C:15]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:14][C:13]=2[CH2:12][CH2:11]3)[CH2:8][CH2:7]1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:27]([O:26][C:15]1[C:16]([CH2:24][CH3:25])=[CH:17][C:18]2[CH:19]3[CH:10]([CH2:11][CH2:12][C:13]=2[CH:14]=1)[CH:9]1[C:22]([CH3:23])([C:6](=[CH:5][CH2:4][OH:3])[CH2:7][CH2:8]1)[CH2:21][CH2:20]3)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66960113HCID 66960113, compound

Product 1

HCID 66960227HCID 66960227, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3-Benzyloxy-2-ethyl-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-ylidene)-acetic acid ethyl ester (0.92 g, 2 mmol) in 20 ml dry THF was cooled to 0° C. under nitrogen before LiAlH4 (0.15 g, 4 mmol) was added in a portion wise manner. After 6 hours at 0° C., the mixture was quenched with aq. NH4Cl, 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 15/1 to 6:1) to give 2-(3-Benzyloxy-2-ethyl-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-ylidene)-ethanol, 0.75 g (89%), as a white powder, mp=61-62° C.; 1H NMR (CDCl3, 270 MHz): 0.84 (s, 3H, CH3), 1.20-1.66 (m, 9H), 1.82-2.02 (m, 3H), 2.21-2.51 (m, 3H), 2.71 (q, J=7.4 Hz, 2H, CH2), 2.87 (m, 2H, H6), 4.16 (m, 2H, CH2OH), 5.07 (s, 2H, CH2Ph), 5.31 (m, 1H, CHCH2OH), 6.66 (s, 1H, ArH), 7.15 (s, 1H, ArH), 7.30-7.48 (m, 5H, Ph).

Workup

  1. additionwas added in a portion wise manner
  2. customthe mixture was quenched with aq. NH4Cl
  3. extractionthe organics were extracted with ethylacetate
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over MgSO4
  6. customthe solvents were evaporated under vacuum
  7. customThe crude oil was purified by chromatography (hexane/ethylacetate 15/1 to 6:1)

Sources & evidence

ORD record
ord-02ed27f975684e0c9779348dba632389
Source dataset
uspto-grants-2011_02
Patent number
US07893284B2

Reaction notes

Loading…