Hexane → HCID 11415144, compound

HRID 1358496Notes

Reaction equation

HRID 1358496 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[CH:13]=[C:12]2[CH2:19][CH2:20][C:21](OCC)=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.CCCCCC.C(=O)=O.CC(C)=O>ClCCl.CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[CH:13]=[C:12]2[CH2:19][CH2:20][CH:21]=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 14487Diisobutylaluminum hydrideHCID 11279149HCID 11279149, compoundHCID 18522661Acetone cardice

Product 1

HCID 11415144HCID 11415144, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Under nitrogen, to a stirred solution of ethyl 3-(5-benzyloxy-1-methylindol-3-yl)propionate (12.0 g, 35.6 mmol) in dichloromethane (120 ml) was added dropwise 1.0 M DIBAL in hexane (37.4 ml, 35.6 mmol) at −78° C. (dry-ice/acetone) for 25 minutes. After 30 minutes, methanol (5.7 ml) was added dropwise at −78° C. and then the mixture was stirred at room temperature for 30 minutes. The mixture was filtered through Celite and washed with dichloromethane. The filtrate was concentrated in vacuo and then the residue was purified by silica gel (90 g) chromatography eluted with toluene/ethyl acetate (10:1 to 5:1) to give 3-(5-benzyloxy-1-methylindol-3-yl)propionaldehyde (8.03 g, 77.0%)

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with dichloromethane
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by silica gel (90 g) chromatography
  5. washeluted with toluene/ethyl acetate (10:1 to 5:1)

Sources & evidence

ORD record
ord-b237e6f307c146d9a656bc3185021a8a
Source dataset
uspto-grants-2003_07
Patent number
US06596738B1

Reaction notes

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