Water → HCID 66660519, compound

HRID 1810599Notes

Reaction equation

HRID 1810599 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][C:40]([C:43]([O:45][CH2:46][CH3:47])=[O:44])=[CH:39][CH:38]=2)=[CH:33][C:32]=1[C:48]1[CH:57]=[CH:56][C:55]2[C:54]([CH3:59])([CH3:58])[CH2:53][CH2:52][C:51]([CH3:61])([CH3:60])[C:50]=2[CH:49]=1)(C(C)(C)C)(C)C.O>O1CCCC1>[OH:26][CH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:38]=[CH:39][C:40]([C:43]([O:45][CH2:46][CH3:47])=[O:44])=[CH:41][CH:42]=2)=[CH:33][C:32]=1[C:48]1[CH:57]=[CH:56][C:55]2[C:54]([CH3:59])([CH3:58])[CH2:53][CH2:52][C:51]([CH3:60])([CH3:61])[C:50]=2[CH:49]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 66660958HCID 66660958, compound

Product 1

HCID 66660519HCID 66660519, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.9 ml (6.9 mmol) of a solution of tetrabutylammonium fluoride (1 M) are added to a solution of 2.75 g (4.6 mmol) of ethyl 4′-[3-(tert-butyldimethylsilanyloxy)propoxy]-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)biphenyl-4-carboxylate in 20 ml of tetrahydrofuran, in a three-necked flask. 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 g of ethyl 4′-(3-hydroxypropoxy)-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)biphenyl-4-carboxylate in the form of a colorless oil (yield=89%).

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-0e12968a3d78419db18d9e1731a0d247
Source dataset
uspto-grants-2013_01
Patent number
US08362082B2

Reaction notes

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