Tetrabutylammonium Fluoride → 1,1-Dimethylethyl 5-(4-biphenylyl)-2-(2-hydroxyethyl)-3-({[4-(methyloxy)phenyl]methyl}oxy)pentanoate

HRID 2382916Notes

Reaction equation

HRID 2382916 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]1([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH:27]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][CH:49]=2)[CH:28]([CH2:36][CH2:37][O:38][Si](C(C)(C)C)(C)C)[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:21][CH:20]=1>O1CCCC1>[C:19]1([C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=2)[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][CH:27]([O:46][CH2:47][C:48]2[CH:49]=[CH:50][C:51]([O:54][CH3:55])=[CH:52][CH:53]=2)[CH:28]([CH2:36][CH2:37][OH:38])[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57887025HCID 57887025, compound

Product 1

HCID 578870221,1-Dimethylethyl 5-(4-biphenylyl)-2-(2-hydroxyethyl)-3-({[4-(methyloxy)phenyl]methyl}oxy)pentanoateYield 58.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tetra-n-butylammonium fluoride (1.0 M in THF; 6.2 mL, 6.2 mmol) was added dropwise over 15 min to a stirred solution of 1,1-dimethylethyl 5-(4-biphenylyl)-2-(2-{[(1,1-dimethylethyl) (dimethyl)silyl]oxy}ethyl)-3-({[4-(methyloxy)phenyl]methyl}oxy)pentanoate (3.39 g, 5.61 mmol) in tetrahydrofuran (20 mL) at 0° C. under nitrogen. The reaction was allowed to warm to room temperature at which stirring was continued for 2 h. The volatiles were evaporated and the residue partitioned between ethyl acetate (100 mL) and water (100 mL). The phases were separated and the aqueous layer was washed with ethyl acetate (3×100 mL). The organic layers were combined, washed with brine (100 mL), dried (magnesium sulfate) and the solvent evaporated. The residue was chromatographed on silica gel (50% to 75% diethyl ether:cyclohexane) to give the title compound (1.6 g, 58%) as a yellow oil which was a mixture of diastereomers. LC/MS: 3.98 min; z/e 491, calcd (M+1) 491. 1H NMR (400 MHz: CDCl3): 7.55 (2H), 7.45 (4H), 7.30 (5H), 6.90 (2H), 4.50 (2H), 3.80 (3H), 3.65 (2H), 2.80 (2H), 2.65 (1H major), 2.05 (1H minor), 1.85 (3H), 1.60-1.35 (11H).

Workup

  1. customThe volatiles were evaporated
  2. customthe residue partitioned between ethyl acetate (100 mL) and water (100 mL)
  3. customThe phases were separated
  4. washthe aqueous layer was washed with ethyl acetate (3×100 mL)
  5. washwashed with brine (100 mL)
  6. dry with materialdried (magnesium sulfate)
  7. customthe solvent evaporated
  8. customThe residue was chromatographed on silica gel (50% to 75% diethyl ether:cyclohexane)

Sources & evidence

ORD record
ord-57cbe4b9ed63469abe696e8442b44f85
Source dataset
uspto-grants-2012_09
Patent number
US08263602B2

Reaction notes

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