Methanol → HCID 67257445, compound

HRID 713825Notes

Reaction equation

HRID 713825 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH2:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][C:16]1([CH3:27])[CH2:20][C:19]2[CH:21]=[CH:22][CH:23]=[C:24]([CH:25]=O)[C:18]=2[O:17]1.CO.[BH4-].[Na+]>C(O)=O>[CH3:15][C:16]1([CH3:27])[CH2:20][C:19]2[CH:21]=[CH:22][CH:23]=[C:24]([CH2:25][NH:14][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:18]=2[O:17]1

Participants

6

Reactant 4

HCID 887MethanolHCID 75899Benzenamine, 2-phenoxy-HCID 27954712,2-Dimethyl-2,3-dihydro-1-benzofuran-7-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 67257445HCID 67257445, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-phenoxy-phenylamine (350 mg, 1.89 mmol) and 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carbaldehyde (500 mg, 2.83 mmol) was heated at 90° C. for 2 h under nitrogen. The reaction was cooled to 0° C. and MeOH (4 mL) was added, followed by NaBH4 (216 mg, 5.70 mmol) in portions over 20 min. The mixture was stirred at room temperature for 24 h. Formic acid (0.4 mL was added and the mixture stirred for 15 min. The solvents were removed in vacuo, the residue quenched with saturated aqueous NaHCO3 (50 mL), extracted with DCM (2×30 mL), dried over MgSO4, filtered and solvents removed in vacuo. The crude material was purified by silica gel chromatography eluting with petroleum spirit (A) and ethyl acetate (B) (5-10% B, 80 g, 3 CV, 60 mL/min) to afford 560 mg (86%) of N-(2,2,-Dimethyl-2,3-dihydrobenzofuran-7-ylmethyl)-N-(2-phenoxy phenyl)amine as a colourless oil.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. stirringthe mixture stirred for 15 min
  3. customThe solvents were removed in vacuo
  4. customthe residue quenched with saturated aqueous NaHCO3 (50 mL)
  5. extractionextracted with DCM (2×30 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customsolvents removed in vacuo
  9. customThe crude material was purified by silica gel chromatography
  10. washeluting with petroleum spirit (A) and ethyl acetate (B) (5-10% B, 80 g, 3 CV, 60 mL/min)

Sources & evidence

ORD record
ord-877dff7360b1473580d2c574613bf545
Source dataset
uspto-grants-2015_11
Patent number
US09186424B2

Reaction notes

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