Tetrabutylammonium Fluoride → HCID 23498888, compound

HRID 1836875Notes

Reaction equation

HRID 1836875 reaction equation
[CH3:1][O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[C:21]([CH2:22][CH2:23][CH2:24][O:25][Si](C(C)(C)C)(C)C)=[CH:20][C:19]3[C:18]([CH3:34])([CH3:33])[CH2:17][CH2:16][C:15]([CH3:36])([CH3:35])[C:14]=3[CH:13]=2)=[CH:6][CH:5]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.O>[CH3:1][O:2][C:3](=[O:37])[C:4]1[CH:5]=[CH:6][C:7](/[CH:10]=[CH:11]/[C:12]2[C:21]([CH2:22][CH2:23][CH2:24][OH:25])=[CH:20][C:19]3[C:18]([CH3:33])([CH3:34])[CH2:17][CH2:16][C:15]([CH3:36])([CH3:35])[C:14]=3[CH:13]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 23518615HCID 23518615, compound

Product 1

HCID 23498888HCID 23498888, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.0 g (7.7 mmol) of Methyl-4-{(E)-2-[3-(3-t-butyldimethylsiloxypropyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl]vinyl}benzoate in 20 mL tetrahydrofuran was added a solution of 8 mL (8.08 mmol) tetrabutylammonium fluoride (1.0 M in tetrahydrofuran). After 30 min the reaction mixture was diluted with water and extracted with ethyl acetate. The organic fraction was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (ethyl acetate) to give 2.67 g (85%) of Methyl-4-{(E)-2-[3-(3-hydroxypropyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl]vinyl}benzoate (m.p.=109-115.5° C.).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic fraction was washed 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 (ethyl acetate)

Sources & evidence

ORD record
ord-2a47dc47ad5d4254b7088fb1b1017d21
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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