Trityl chloride → 2-triphenylmethoxymethyl-2-propen-1-ol

HRID 931840Notes

Reaction equation

HRID 931840 reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]=[C:22]([CH2:25][OH:26])[CH2:23][OH:24].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.C(OCC)(=O)C>[C:2]1([C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:24][CH2:23][C:22](=[CH2:21])[CH2:25][OH:26])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 770481,3-Propanediol, 2-methylene-HCID 516892Sodium Bicarbonate

Product 1

HCID 111633262-triphenylmethoxymethyl-2-propen-1-olYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of trityl chloride (4.05 g; 14.3 mmol) and 2-methylenepropane-1,3-diol (1.20 mL; 14.3 mmol) in dry CH2Cl2 (20 mL) was added triethylamine (4.0 mL; 28.5 mmol) slowly at room temperature. The reaction was stirred at room temperature for 1 h and then ethyl acetate (100 mL) and saturated aqueous NaHCO3 (30 mL) were added. The organic layer was separated and washed by saturated aqueous NaHCO3 and NaCl respectively, and dried over anhydrous Na2SO4. After evaporation of the solvent, the residue was purified by flash column chromatography over silica gel using ethyl acetate-hexane (1:10.5) as the eluent to afford 10 as white solid (2.89 g; 62% yield): 1H NMR (400 MHz, CDCl3) δ 7.42-7.48 (m, 6H, six of ArH), 7.27-7.33 (m, 6H, six of ArH), 7.20-7.27 (m, 3H, three of ArH), 5.26 (s, 1H, one of C═CH2), 5.17 (s, 1H, one of C═CH2), 4.13 (d, J=6.1 Hz, 2H, CH2OH), 3.70 (s, 2H, Ph3COCH2), 1.72 (t, J=6.1 Hz, 1H, CH2OH); 13C NMR (100 MHz, CDCl3) δ 145.4, 143.6, 128.3, 127.6, 126.8, 111.6, 87.0, 65.3, 64.5, (8).

Workup

  1. customThe organic layer was separated
  2. washwashed by saturated aqueous NaHCO3 and NaCl respectively
  3. dry with materialdried over anhydrous Na2SO4
  4. customAfter evaporation of the solvent
  5. customthe residue was purified by flash column chromatography over silica gel

Sources & evidence

ORD record
ord-08dd16f0783849c99bd8856b4ce6c230
Source dataset
uspto-grants-2016_03
Patent number
US09297042B2

Reaction notes

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