Methanol → HCID 18789965, compound

HRID 1106889Notes

Reaction equation

HRID 1106889 reaction equation
[CH2:1]([O:8][C:9]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:10]=1[O:11][CH2:12][C:13](OCC)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].CO.O>C1COCC1>[CH2:1]([O:8][C:9]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:10]=1[O:11][CH2:12][CH2:13][OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 54352603HCID 54352603, compound

Product 1

HCID 18789965HCID 18789965, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (2-benzyloxy-4-nitrophenoxy)acetate (800 mg, 4.83 mmol) was dissolved in THF (50 ml); thereafter, sodium borohydride (457 mg, 12.1 mmol) was added and the mixture was heated to the reflux temperature. At the same temperature, methanol (5 ml) was slowly added dropwise over 30 min, followed by stirring at the reflux temperature for 30 min. The reaction solution was cooled to room temperature and water (10 ml) was added, followed by extraction with ethyl acetate (200 ml). The extracted organic layer was dried with magnesium sulfate and the solvent was evaporated; the resulting residue was purified by being subjected to column chromatography on silica gel using a 1:1 solvent system on n-hexane and ethyl acetate as an eluent. The fractions containing the product were collected and the solvent was evaporated to yield the end compound 2-(2-benzyloxy-4-nitrophenoxy)ethanol (400 ml).

Workup

  1. temperaturethe mixture was heated to the reflux temperature
  2. extractionfollowed by extraction with ethyl acetate (200 ml)
  3. dry with materialThe extracted organic layer was dried with magnesium sulfate
  4. customthe solvent was evaporated
  5. customthe resulting residue was purified
  6. additionThe fractions containing the product
  7. customwere collected
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-159168b1675648f0a685e82ecddd1b28
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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