Acetic Acid → HCID 23518589, compound

HRID 1836873Notes

Reaction equation

HRID 1836873 reaction equation
[C:1]([C:3]1[C:12]([CH2:13][CH2:14][CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])=[CH:11][C:10]2[C:9]([CH3:25])([CH3:24])[CH2:8][CH2:7][C:6]([CH3:27])([CH3:26])[C:5]=2[CH:4]=1)#N.[H-].C([Al+]CC(C)C)C(C)C.C(O)(=[O:40])C.O>ClCCl>[CH:1]([C:3]1[C:12]([CH2:13][CH2:14][CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])=[CH:11][C:10]2[C:9]([CH3:25])([CH3:24])[CH2:8][CH2:7][C:6]([CH3:27])([CH3:26])[C:5]=2[CH:4]=1)=[O:40]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 23518590HCID 23518590, compound

Product 1

HCID 23518589HCID 23518589, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4.6 g (11.9 mmol) of 2-cyano-3-(3-t-butyldimethylsiloxypropyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene.in 40 mL of dichloromethane at −78° C. was added 17.9 mL (17.9 mmol) of diisobutylaluminum hydride (1.0 M in toluene). The reaction mixture was stirred and allowed to slowly warm to room temperature. After 16 hours, acetic acid was added dropwise, followed by addition of water and dichloromethane. The organic fraction was separated, washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (gradient elution: 4-25% ethyl acetate/hexane) to afford 2.48 g (53%) of 2-formyl -3-(3-t-butyldimethylsiloxypropyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene. M+=389).

Workup

  1. customThe organic fraction was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel (gradient elution: 4-25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2b36436f8b504189b098437261494080
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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