Aluminium lithium hydride → HCID 59858085, compound

HRID 2378375Notes

Reaction equation

HRID 2378375 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1([CH3:24])[CH2:15][CH2:14][C:13]2[C:8](=[C:9]3[CH:20]4[CH2:21][CH2:22][CH2:23][CH:17]([CH2:18][CH2:19]4)[C:10]3=[C:11]([OH:16])[CH:12]=2)[O:7]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:2][CH2:3][CH2:4][CH2:5][C:6]1([CH3:24])[CH2:15][CH2:14][C:13]2[C:8](=[C:9]3[CH:20]4[CH2:21][CH2:22][CH2:23][CH:17]([CH2:18][CH2:19]4)[C:10]3=[C:11]([OH:16])[CH:12]=2)[O:7]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57765644HCID 57765644, compound

Product 1

HCID 59858085HCID 59858085, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(6-hydroxy-2-methyl-3,4,7,8,9,10-hexahydro-7,10-propano-2H-benzo[h]chromen-2-yl)-propionic acid methyl ester (212 mg, 0.61 mmol) in 50 mL dry THF was added LiAlH4 in 8 portions over a period of 20 min. The reaction was stirred for 2 h and quenched onto ice (80 g). The mixture was extracted with EtOAc (3×50 mL) and combined organic layers were dried over Na2SO4 and concentrated. The crude product was chromatographed (hexane/EtOAc=6:1) to yield 2-(3-hydroxy-propyl)-2-methyl-3,4,7,8,9,10-hexahydro-7,10-propano-2H-benzo[h]chromen-6-ol as a light yellow oil (169 mg). 1H-NMR (CDCl3, 300 MHz) δ (ppm): 6.39 (s, 1 H), 5.78 (s, 1 H), 3.69 (m, 2 H), 3.54 (m, 1 H), 3.40 (m, 1 H), 2.69 (m, 2 H), 2.45 (ws, 1 H), 1.90-1.60 (m, 14 H), 1.26 (m, 5 H); 13C-NMR δ (ppm): 144.3, 142.9, 132.7, 128.9, 118.6, 112.6, 75.0, 63.3, 36.1, 35.7, 32.1, 32.0, 31.9, 29.4, 28.7, 26.8, 26.4, 26.1, 24.2, 23.6, 22.8, 22.4; MS (ESI) m/z: 317 (M+H+, 100%).

Workup

  1. customquenched onto ice (80 g)
  2. extractionThe mixture was extracted with EtOAc (3×50 mL)
  3. dry with materialwere dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was chromatographed (hexane/EtOAc=6:1)

Sources & evidence

ORD record
ord-5a60c451105f4ad89e5b301d72fb2b08
Source dataset
uspto-grants-2008_12
Patent number
US07470798B2

Reaction notes

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