Aluminium lithium hydride → HCID 86587688, compound

HRID 2416280Notes

Reaction equation

HRID 2416280 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CON(C)[C:10]([CH:12]1[CH2:14][CH:13]1[C:15]1[C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[S:18][CH:19]=1)=[O:11]>O1CCCC1>[S:18]1[CH:19]=[C:15]([C@@H:13]2[CH2:14][C@H:12]2[CH:10]=[O:11])[C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]1=2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23518976HCID 23518976, compound

Product 1

HCID 86587688HCID 86587688, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

Powdered lithium aluminum hydride (3.05 g, 80.4 mmol) was carefully added portionwise to a stirred solution of 2-benzo[b]thiophen-3-yl-cyclopropanecarboxylic acid methoxy-methyl-amide (3.50 g, 13.4 mmol) in anhydrous tetrahydrofuran (300 ml) at −40° C. under N2. The resulting mixture was stirred at −40° C. for 3 h. The reaction was quenched with ethyl acetate (100 ml) and allowed to warmed to room temperature. After 20 min, water (5 ml) was added followed by a solution of aqueous sodium hydroxide (5N, 5 ml). After stirring for 30 min at room temperature the aluminum salts were removed by vacuum filtration. The salts were washed with ethyl acetate (100 ml) and the combined filtrates were concentrated in vacuo. The crude material was purified by silica gel column chromatography (10% ethyl acetate in hexane) to give trans-2-benzo[b]thiophen-3-yl-cyclopropanecarbaldehyde (2.02 g, 75%). 1H NMR (500 MHz, CDCl3) 9.48 (1H, d, J=4.57 Hz), 7.84 (2H, dd, J=17.09, 7.33 Hz), 7.41 (2H, m), 2.80 (1H, m), 2.17 (1H, m), 1.78 (1H, m), 1.59 (1H, m); MS m/e 203.22 (M+H)+.

Workup

  1. customThe reaction was quenched with ethyl acetate (100 ml)
  2. temperatureallowed to warmed to room temperature
  3. waitAfter 20 min
  4. additionwater (5 ml) was added
  5. stirringAfter stirring for 30 min at room temperature the aluminum salts
  6. customwere removed by vacuum filtration
  7. washThe salts were washed with ethyl acetate (100 ml)
  8. concentrationthe combined filtrates were concentrated in vacuo
  9. customThe crude material was purified by silica gel column chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-643d7484dc934b9a8b5b43e39b3b4fda
Source dataset
uspto-grants-2004_11
Patent number
US06822100B2

Reaction notes

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