Methanol → 3-(2-Hydroxy-4-methoxy-5-thiocyanato-phenyl)-propionic acid methyl ester

HRID 984114

Reaction equation

HRID 984114 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:13])[O:10]2)=[CH:5][CH:4]=1.[C:14]([S-:16])#[N:15].[K+].BrBr.[CH3:20][OH:21]>>[CH3:20][O:21][C:9](=[O:13])[CH2:8][CH2:7][C:6]1[CH:5]=[C:4]([S:16][C:14]#[N:15])[C:3]([O:2][CH3:1])=[CH:12][C:11]=1[OH:10]

Participants

5

Reactant 4

HCID 887MethanolHCID 24408BromineHCID 516872Potassium thiocyanateHCID 123898377-Methoxychroman-2-one

Product 1

HCID 207659993-(2-Hydroxy-4-methoxy-5-thiocyanato-phenyl)-propionic acid methyl ester

Procedure

Compound 14A (3 g), KSCN (4.9 g) were dissolved in MeOH (125 mL) at 0° C., Br2 (3 g) was added, then stirred for 2 h. The reaction mixture was quenched with water (200 mL) and ethyl acetate (200 mL). The ethyl acetate was separated and washed with water, brine, dried (MgSO4), concentrated, to afford compound 14B (3.5 g). mp 105-016° C.; MS: 268 (M+1)+. Preparation of 6-Mercapto-7-methoxy-chroman-2-ol (Compound 14C)

Workup

  1. customThe reaction mixture was quenched with water (200 mL) and ethyl acetate (200 mL)
  2. customThe ethyl acetate was separated
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-48c920a6ff2048748cf5783424bcecc1
Source dataset
uspto-grants-2005_03
Patent number
US06867224B2

Linked notes

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