Sodium borohydride → Methyl 4-[4-(1-hydroxyethyl)-2-methoxy-5-nitrophenoxy]butyrate

HRID 1584532Notes

Reaction equation

HRID 1584532 reaction equation
[C:1]([C:4]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:6]([O:21][CH3:22])[CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO.Cl>[OH:3][CH:1]([C:4]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:6]([O:21][CH3:22])[CH:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 10733790HCID 10733790, compound

Product 1

HCID 10591264Methyl 4-[4-(1-hydroxyethyl)-2-methoxy-5-nitrophenoxy]butyrate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 4-(4-acetyl-2-methoxy-5-nitrophenoxy)butyrate (5.06 g) in methanol (300 cm3) was cooled with stirring at 0° C. under argon. Sodium borohydride (640 mg) was added portionwise and the resulting solution stirred at 40° C. overnight. Further sodium borohydride (500 mg) was added as TLC analysis indicated that starting material remained. After a further 3 h TLC analysis indicated that the reaction was complete. The reaction was cooled, acidified with dilute (1M) hydrochloric acid and evaporated to dryness. The residue was dissolved in ethyl acetate (250 cm3) washed with dilute aqueous acid and brine, dried over magnesium sulphate and filtered. The solvent was evaporated to leave a yellow oil which solidified on standing. After recrystallisation from methanol/diethyl ether, methyl 4-[4-(1-hydroxyethyl)-2-methoxy-5-nitrophenoxy]butyrate was obtained as yellow needles (5.04 g, ~100%). 1H NMR (CDCl3) δ1.52 (3H, d, J=8.3 Hz, MeCHO), 2.18 (2H, m, CCH2C), 2.53 (2H, t, J=6.5 Hz, CH2CO), 3.71 (3H, s, OMe), 3.95 (3H, s, OMe), 4.13 (2H, t, J=7.3 Hz, CH2O), 5.52 (1H, q, J=8.2 Hz, CHOH), 7.29 (1H, s, aromatic) and 7.57 (1H, s, aromatic).

Workup

  1. stirringthe resulting solution stirred at 40° C. overnight
  2. temperatureThe reaction was cooled
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in ethyl acetate (250 cm3)
  5. washwashed with dilute aqueous acid and brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customThe solvent was evaporated
  9. customto leave a yellow oil which
  10. customAfter recrystallisation from methanol/diethyl ether

Sources & evidence

ORD record
ord-8e197423e35b4c89998e0d56c2708160
Source dataset
uspto-grants-1999_08
Patent number
US05932695

Reaction notes

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