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

HRID 2069010Notes

Reaction equation

HRID 2069010 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 stirred solution of trityl chloride (4.05 g; 14.3 mmol) and 2-methylenepropane-1,3-diol 1 (1.20 mL; 14.3 mmol) in dry CH2Cl2 (20 mL), triethylamine (4.0 mL; 28.5 mmol) was added slowly at room temperature. The mixture was stirred at room temperature for 1 h, and then ethyl acetate (100 mL) and saturated aqueous NaHCO3 (30 mL) were added. The organic phase was washed with saturated aqueous NaHCO3, NaCl, and dried over anhydrous Na2SO4. After evaporation, the residue was purified by flash column chromatography using ethyl acetate-hexane (1:10˜5) as the eluent to afford 2 as a white solid (2.89 g; 62% yield): 1H NMR (400 MHz, CDCl2) 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.

Workup

  1. washThe organic phase was washed with saturated aqueous NaHCO3, NaCl
  2. dry with materialdried over anhydrous Na2SO4
  3. customAfter evaporation
  4. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-f5d1cd2d6a6a4a43b7949e298e89aad0
Source dataset
uspto-grants-2012_10
Patent number
US08298792B2

Reaction notes

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