Water → 2-(5-Hydroxy-6,7-dimethyl-benzofuran-2-yl)-4-methyl-morpholin-2-ol

HRID 480983Notes

Reaction equation

HRID 480983 reaction equation
Br[CH2:2][C:3]([C:5]1[O:6][C:7]2[C:13]([CH3:14])=[C:12]([CH3:15])[C:11]([O:16]C(=O)C)=[CH:10][C:8]=2[CH:9]=1)=[O:4].[CH3:20][NH:21][CH:22](O)[CH3:23].C(=O)([O-])[O-:26].[K+].[K+].O>CC(C)=O>[OH:16][C:11]1[C:12]([CH3:15])=[C:13]([CH3:14])[C:7]2[O:6][C:5]([C:3]3([OH:4])[O:26][CH2:23][CH2:22][N:21]([CH3:20])[CH2:2]3)=[CH:9][C:8]=2[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5247031N-MethylaminoethanolHCID 101719982-Bromo-1-(5-acetoxy-6,7-dimethyl-benzofuran-2-yl)-ethanone

Product 1

HCID 121121262-(5-Hydroxy-6,7-dimethyl-benzofuran-2-yl)-4-methyl-morpholin-2-olYield 78.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-bromo-1-(5-acetoxy-6,7-dimethyl-benzofuran-2-yl)-ethanone (30 mg), methylaminoethanol (7 mg), and potassium carbonate (20 mg) in acetone (10 mL) was stirred at RT for 1 h. The mixture was poured into water and extracted with ethylacetate. The organic layer was dried and evaporated followed by purification by silica gel column chromatography eluting with 5% MeOH in DCM to give 20 mg of 2-(5-hydroxy-6,7-dimethyl-benzofuran-2-yl)-4-methyl-morpholin-2-ol as an oil, and was converted into the HCl salt. The NMR showed an equilibrium of the hemiketal and ketone form. 1H NMR (CDCl3, 300 MHz) δ: 7.51, 7.26 (2s, combined, 1H), 7.06, 6.87 (2s, combined 1H), 7.06, 6.87 (2s, combined 1H) 4.2-3.7 (m, 2H), 3.2-2.8 (m, 4H), 2.5-2.0 (m, 12H) ppm. 13C NMR (CDCl3, 75 MHz) δ: 189.26, 170.43, 170.18, 156.79, 152.53, 145.71, 125.79, 125.39, 124.46, 121.73, 113.88, 113.14, 111.52, 104.28, 92.48, 63.55, 62.62, 61.11, 59.68, 54.75, 46.37, 21.30, 13.48, 13.02, 12.90 ppm. M/S 320 (M+H+).

Workup

  1. extractionextracted with ethylacetate
  2. customThe organic layer was dried
  3. customevaporated
  4. customfollowed by purification by silica gel column chromatography
  5. washeluting with 5% MeOH in DCM

Sources & evidence

ORD record
ord-d68e632e2eb3449397673fe103d24562
Source dataset
uspto-grants-2003_11
Patent number
US06653346B1

Reaction notes

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