Ethyl Acetate → HCID 59350828, compound

HRID 1644747Notes

Reaction equation

HRID 1644747 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[C:20]([CH3:21])=[C:19]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH2:32][CH3:33])(=[O:31])=[O:30])=[CH:25][CH:24]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:34])[CH:17]=2)[CH:12]=1)=O.C(OCC)(=O)C>O1CCCC1>[CH2:32]([S:29]([C:26]1[CH:27]=[CH:28][C:23]([CH2:22][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([F:34])[CH:17]=3)[CH:12]=[C:11]([CH2:9][OH:8])[C:20]=2[CH3:21])=[CH:24][CH:25]=1)(=[O:30])=[O:31])[CH3:33]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 59350843HCID 59350843, compound

Product 1

HCID 59350828HCID 59350828, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of lithium aluminum hydride (399 mg, 10.5 mmol) in tetrahydrofuran (25 mL) was cooled to 0° C. under a stream of argon. A solution of 4-(4-ethanesulfonyl-benzyl)-6-fluoro-3-methyl-naphthalene-2-carboxylic acid methyl ester (870 mg, 2.18 mmol) in tetrahydrofuran (30 mL) was added slowly drop-wise to the 0° C. suspension. The reaction mixture was stirred at 0° C. for 15 minutes. The reaction mixture was warmed to room temperature and it was stirred at room temperature for 15 minutes. The reaction mixture was cooled again to 0° C. Ethyl acetate was added drop-wise to quench the unreacted lithium aluminum hydride. A saturated aqueous solution of potassium sodium tartrate was added. The organic phase was separated, dried over MgSO4, filtered, and concentrated to afford 780 mg (96%) of [4-(4-ethanesulfonyl-benzyl)-6-fluoro-3-methyl-naphthalen-2-yl]-methanol as an oily white solid. This product was used in subsequent reactions without further purification. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.98 (dd, J=8.9, 6.2 Hz, 1 H), 7.90 (s, 1 H), 7.73 (d, J=8.2 Hz, 2 H), 7.67 (d, J=12.4 Hz, 1 H), 7.34 (dd, J=8.9, 2.1 Hz, 1 H), 7.29 (d, J=8.2 Hz, 2 H), 5.27 (t, J=5.1 Hz, 1 H), 4.66 (d, J=5.1 Hz, 2 H), 4.58 (s, 2 H), 3.20 (q, J=7.2 Hz, 2 H), 2.31 (s, 3 H), 1.04 (t, J=7.2 Hz, 3 H). HRMS (ES+) cald. for C21H21FO3S [(M+Na)+] 395.1087, obsd. 395.1088.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. stirringit was stirred at room temperature for 15 minutes
  3. temperatureThe reaction mixture was cooled again to 0° C
  4. customto quench the unreacted lithium aluminum hydride
  5. additionA saturated aqueous solution of potassium sodium tartrate was added
  6. customThe organic phase was separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-92258918df8e438ca88dda583a73b76a
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

Loading…