Water → HCID 67542123, compound

HRID 1809821Notes

Reaction equation

HRID 1809821 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][OH:12].[CH3:13]N(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.O>C(Cl)Cl>[CH3:13][O:12][CH2:11][CH2:10][CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][OH:1]

Participants

5

Reactant 3

HCID 962WaterHCID 88675Proton spongeHCID 10419543Benzenepropanol, 2-(hydroxymethyl)- (9CI)

Product 1

HCID 67542123HCID 67542123, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of the title A compound, 3-(2-hydroxymethyl-phenyl)-propan-1-ol (14.9 g, 90 mmol) and proton-sponge (25 g, 1.3 eq.) in methylene chloride (500 mL) is added at 0° C. under nitrogen trimethyloxonium-tetrafluoroborate (17.3 g, 117 mmol). The reaction mixture is further stirred for 5 h at room temperature before filtration. The filtrate is poured into water and the aqueous layer extracted twice with methylene chloride. The combined organic extracts are dried over Na2SO4, filtered and concentrated under reduced pressure. The residue is purified by flash column chromatography on silica gel (hexane/EtOAc 7/3 to 1/1 and to AcOEt/MeOH 9/1) to afford the title compound: TLC, Rf (hexane/AcOEt 4/1)=0.57. MS 198.0 [M+18].

Workup

  1. additionis added at 0° C. under nitrogen trimethyloxonium-tetrafluoroborate (17.3 g, 117 mmol)
  2. extractionthe aqueous layer extracted twice with methylene chloride
  3. dry with materialThe combined organic extracts are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by flash column chromatography on silica gel (hexane/EtOAc 7/3 to 1/1 and to AcOEt/MeOH 9/1)

Sources & evidence

ORD record
ord-5eec32501cac4ca1bede7057d759022a
Source dataset
uspto-grants-2013_01
Patent number
US08362040B2

Reaction notes

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