Water → HCID 86718027, compound

HRID 1500489Notes

Reaction equation

HRID 1500489 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N+:13]([O-:15])=[O:14])[C:5]2[O:9][CH:8]([CH2:10][OH:11])[CH2:7][C:6]=2[CH:12]=1.[H-].[Na+].[CH3:18]I.O>C1COCC1>[CH3:18][O:11][CH2:10][CH:8]1[CH2:7][C:6]2[CH:12]=[C:2]([CH3:1])[CH:3]=[C:4]([N+:13]([O-:15])=[O:14])[C:5]=2[O:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86718021HCID 86718021, compound

Product 1

HCID 86718027HCID 86718027, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (5-methyl-7-nitro-2,3-dihydrobenzofuran-2-yl)methanol (0.70 g, 3.3 mmol) in THF was cooled to 0° C. NaH was added to the mixture at 0° C. It was stirred for 15 min at 0° C. MeI was added dropwise to the mixture at 0° C. It was stirred for 0.5 h at 0° C. The mixture was poured into water (20 mL), extracted with EtOAc (40 mL), washed with water, brine, dried and concentrated to give the title compound (8a) as a yellow oil. MS-ESI (m/z): 224 (M+1)+.

Workup

  1. stirringIt was stirred for 0.5 h at 0° C
  2. extractionextracted with EtOAc (40 mL)
  3. washwashed with water, brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6e3901bd6c66407480571f38384e31d1
Source dataset
uspto-grants-2015_12
Patent number
US09206166B2

Reaction notes

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