Water → HCID 66660890, compound

HRID 1810601Notes

Reaction equation

HRID 1810601 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][C:41]([C:44]([O:46][CH2:47][CH3:48])=[O:45])=[CH:40][CH:39]=2)=[CH:34][C:33]=1[C:49]1[CH:58]=[CH:57][C:56]2[C:55]([CH3:60])([CH3:59])[CH2:54][CH2:53][C:52]([CH3:62])([CH3:61])[C:51]=2[CH:50]=1)(C(C)(C)C)(C)C.O>O1CCCC1>[OH:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][C:41]([C:44]([O:46][CH2:47][CH3:48])=[O:45])=[CH:40][CH:39]=2)=[CH:34][C:33]=1[C:49]1[CH:58]=[CH:57][C:56]2[C:55]([CH3:60])([CH3:59])[CH2:54][CH2:53][C:52]([CH3:61])([CH3:62])[C:51]=2[CH:50]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 66660750HCID 66660750, compound

Product 1

HCID 66660890HCID 66660890, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.8 ml (6.8 mmol) of a solution of tetrabutylammonium fluoride (1 M) are added to a solution of 2.8 g (4.5 mmol) of ethyl 4′-[4-(tert-butyldimethylsilanyloxy)butoxy]-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)biphenyl-4-carboxylate in 20 ml of tetrahydrofuran. The reaction mixture is stirred for 4 h at ambient temperature. The reaction is stopped by adding 20 ml of water and the mixture is then extracted with ethyl acetate. The organic phases are combined, washed with a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. The solvents are evaporated off. The crude obtained in the form of an oil is chromatographed on silica gel (heptane/ethyl acetate: 70/30), to give 2.10 g of ethyl 4′-(4-hydroxybutoxy)-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)biphenyl-4-carboxylate in the form of a colorless oil (yield=93%).

Workup

  1. extractionthe mixture is then extracted with ethyl acetate
  2. washwashed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customThe solvents are evaporated off
  5. customThe crude obtained in the form of an oil
  6. customis chromatographed on silica gel (heptane/ethyl acetate: 70/30)

Sources & evidence

ORD record
ord-d3888da99f0b4d5f960e9ef91e5c31ab
Source dataset
uspto-grants-2013_01
Patent number
US08362082B2

Reaction notes

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