Diisopropylamine → Tert-butyl 3-hydroxy-3-[2-(8-phenyloctyl)phenyl]propionate

HRID 2082610Notes

Reaction equation

HRID 2082610 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH3:14].[C:21]1([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]2[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=2[CH:37]=[O:38])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1.CCCCCC.O1CCCC1>[OH:38][CH:37]([C:36]1[CH:39]=[CH:40][CH:41]=[CH:42][C:35]=1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:14][C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 10908tert-Butyl acetateHCID 98176132-(8-Phenyloctyl)benzaldehydeHCID 178418339Butyllithium

Product 1

HCID 15617420Tert-butyl 3-hydroxy-3-[2-(8-phenyloctyl)phenyl]propionate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21883165Tetrahydrofuran hexaneSolvent

Procedure

A solution of diisopropylamine (4.8 ml, 0.03 mole) in tetrahydrofuran/hexane (100 ml, 1/1) was cooled to -60° C. and n-butyllithium (2.5M solution in hexane, 13.6 ml, 0.03 mole) was added. This solution was stirred for 10 minutes followed by addition of t-butyl acetate (4.6 ml, 0.03 mole). The mixture was stirred for an additional 10 minutes before addition of a solution of 2-(8-phenyloctyl)benzaldehyde (10 gm, 0.03 mole) in tetrahydrofuran (25 ml) was added dropwise. The whole was stirred first for 30 minutes at -50° C. and then for 30 minutes at -20° C. The reaction, mixture was poured into aqueous acid and extracted twice with diethyl ether. The combined extracts were washed with 5% aqueous sodium bicarbonate solution and saturated aqueous sodium chloride sodium and then dried over anhydrous magnesium sulfate, filtered and evaporated. Chromatography on silica gel using hexane-ethyl acetate (95/5) to elute gave the product as an oil. 90 MHz NMR (CDCl3) δ1.29-1.52 (12 H,m) 2.52-2.78 (6 H,m) 5.39 (1 H,dd) 7.10-7.60 (9 H,m).

Workup

  1. additionwas added dropwise
  2. stirringThe whole was stirred first for 30 minutes at -50° C.
  3. waitfor 30 minutes at -20° C
  4. customThe reaction, mixture
  5. additionwas poured into aqueous acid
  6. extractionextracted twice with diethyl ether
  7. washThe combined extracts were washed with 5% aqueous sodium bicarbonate solution and saturated aqueous sodium chloride sodium
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. washto elute

Sources & evidence

ORD record
ord-2b61d5f80c6449498063efc42648c3ea
Source dataset
uspto-grants-1993_02
Patent number
US05189226

Reaction notes

Loading…