Sodium Hydroxide → 2-triphenylmethoxymethyl-2-propen-1-ol

HRID 931843Notes

Reaction equation

HRID 931843 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].[C:11]1([C:17]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:18][CH2:19][C:20](=[CH2:24])[CH2:21]C#N)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-:37].[Na+]>CCOCC>[C:31]1([C:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[O:18][CH2:19][C:20](=[CH2:24])[CH2:21][OH:37])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 57915012HCID 57915012, compound

Product 1

HCID 111633262-triphenylmethoxymethyl-2-propen-1-olYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of LiAlH4 (119 mg; 2.98 mmol) in dry ether (5 mL), AlCl3 (400 mg; 2.94 mmol) was added carefully at 0° C. and the mixture was stirred for 15 min. Then a solution of 12 (829 mg; 2.44 mmol) in dry ether (9 mL) was added and the reaction was stirred at 0° C. for 3 h. After that 10% aqueous NaOH (10 mL) was added to quench the reaction. The organic layer was separated and washed by saturated aqueous NaHCO3 and NaCl respectively, and dried over anhydrous K2CO3. After evaporation of the solvent, the residue was purified by flash column chromatography over silica gel using CH3OH—CH2Cl2 (1:205) as the eluent to afford 10 as colorless oil (545 mg; 65% yield): 1H NMR (400 MHz, CDCl3) δ 7.41-7.48 (m, 6H, six of ArH), 7.26-7.33 (m, 6H, six of ArH), 7.19-7.26 (m, 3H, three of ArH), 5.33 (s, 1H, one of C═CH2), 4.96 (s, 1H, one of C═CH2), 3.53 (s, 2H, Ph3COCH2), 2.70 (m, 2H, CH2CH2NH2) 2.18 (t, J=6.7 Hz, 2H, CH2CH2NH2), 2.06 (br s, 2H, NH2); 13C NMR (100 MHz, CDCl3) δ 143.6, 143.4, 128.1, 127.4, 126.5, 111.3, 86.5, 66.1, 39.8, 37.4; HRMS (FAB+) calcd for C24H26ON (M+H+): 344.2014. found: 344.2017, (11).

Workup

  1. stirringthe reaction was stirred at 0° C. for 3 h
  2. customto quench
  3. customthe reaction
  4. customThe organic layer was separated
  5. washwashed by saturated aqueous NaHCO3 and NaCl respectively
  6. dry with materialdried over anhydrous K2CO3
  7. customAfter evaporation of the solvent
  8. customthe residue was purified by flash column chromatography over silica gel

Sources & evidence

ORD record
ord-51d1c6eb6c424b7785b25921eee4e54a
Source dataset
uspto-grants-2016_03
Patent number
US09297042B2

Reaction notes

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