Trityl chloride → (2R)-1-(triphenylmethoxy)-2-propanol

HRID 1958909Notes

Reaction equation

HRID 1958909 reaction equation
[CH2:1]([OH:5])[C@H:2]([OH:4])[CH3:3].C(N(CC)CC)C.Cl[C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:15]1([C:14]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[O:5][CH2:1][C@H:2]([OH:4])[CH3:3])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 259994R-(-)-1,2-Propanediol

Product 1

HCID 11067110(2R)-1-(triphenylmethoxy)-2-propanol

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent2×

Procedure

To a suspension of (2R)-1,2-propanediol (1.9 mL) in toluene (20 mL) was added triethylamine (8.3 mL) and 4-dimethylaminopyridine (32 mg). The mixture was ice-cooled and 1,1′,1″-(chloromethylidyne)tris-benzene (6.6 g) was added and the mixture stirred at ambient temperature for 20 h. The reaction mixture was diluted with toluene then extracted with ammonium chloride solution (×2), then brine (×1) and the organic layer was dried (MgSO4), filtered and evaporated. The resulting oil was triturated with iso-hexane to give subtitle compound as a white solid. Yield: 4 g

Workup

  1. temperaturecooled
  2. extractionthen extracted with ammonium chloride solution (×2)
  3. dry with materialbrine (×1) and the organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting oil was triturated with iso-hexane

Sources & evidence

ORD record
ord-d0d47b092ad9479f9c08105723fb9c4f
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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