Aluminium lithium hydride → HCID 22640074, compound

HRID 2415047Notes

Reaction equation

HRID 2415047 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH:11]([CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=1)C>CCOCC>[OH:9][CH2:10][CH:11]([CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[C:17]([O:25][CH3:26])[C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 22640073HCID 22640073, compound

Product 1

HCID 22640074HCID 22640074, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of lithium aluminum hydride (1.0 M in tetrahydrofuran, 2.00 mL, 2.00 mmol) was added dropwise to a solution of ethyl-2-(3-phenylpropyl)-5-(3,4,5-trimethoxyphenyl)pentanoate (1.39 g, 3.36 mmol) in ether (30 mL) at 0° C. After 30 min., a second aliquot of lithium aluminum hydride (1.0 M in tetrahydrofuran, 1.00 mL, 1.00 mmol) was added and the resulting solution was stirred for 30 minutes. Rochelles salt (1 M, 40 mL) was added and the mixture was stirred vigorously for 1.5 h. The aqueous layer was extracted with ether and the combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified silica gel chromatography, eluting with 50% ethyl acetate/hexanes, to yield 4-hydroxymethyl-7-phenyl-1-(3,4,5-trimethoxyphenyl)heptane (1.23 g, 98%). 1H NMR (300 MHz, CDCl3): δ 1.36 (m, 5 H), 1.60 (m, 5 H), 2.56 (t, 2 H, J=7.7), 2.63 (t, 2 H, J=7.7), 3.58 (d, 2 H, J=5.3), 3.84 (s, 3 H), 3.86 (s, 6 H), 6.40 (s, 2 H), 7.25 (m, 5 H).

Workup

  1. stirringthe mixture was stirred vigorously for 1.5 h
  2. extractionThe aqueous layer was extracted with ether
  3. dry with materialthe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified silica gel chromatography
  6. washeluting with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-8db0df8c0e194a47ad6eeefb6e954ba7
Source dataset
uspto-grants-2004_11
Patent number
US06818643B1

Reaction notes

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