Sodium borohydride → HCID 117641987, compound

HRID 1048734Notes

Reaction equation

HRID 1048734 reaction equation
[BH4-].[Na+].[Cl:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([N+:16]([O-:18])=[O:17])=[C:12]([CH:15]=1)[CH:13]=[O:14]>CO>[Cl:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([N+:16]([O-:18])=[O:17])=[C:12]([CH2:13][OH:14])[CH:15]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23318827HCID 23318827, compound

Product 1

HCID 117641987HCID 117641987, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (133 mg, 0.00351 moles) was added to 5-(3-chloropropoxy)-2-nitrobenzaldehyde (570 mg, 0.00234 moles) in anhydrous methanol (12 mL) at 0° C. under nitrogen. The reaction was stirred for 1.5 hours and then concentrated with a rotary evaporator. The mixture was diluted with ethyl acetate (75 mL) and washed with 30 mL each of saturated sodium bicarbonate solution, water, and brine. The organic layer was dried with anhydrous magnesium sulfate, which was removed by filtration. The filtrate was concentrated, and the resulting residue was subject to silica gel chromatography using a gradient of 100% hexanes to 60% ethyl acetate in hexanes. The fractions containing the product were collected and volatiles were removed by rotary evaporation. The resulting residue was dried overnight to yield (5-(3-chloropropoxy)-2-nitrophenyl)methanol as a pale yellow solid (yield 69%*). 1H NMR (400 MHz, CD2Cl2) δ 8.16 (d, J=9.1 Hz, 1H), 7.27 (d, J=2.7 Hz, 1H), 6.92 (dd, J=9.1, 2.8 Hz, 1H), 4.98 (s, 2H), 4.24 (t, J=5.9 Hz, 2H), 3.77 (t, J=6.3 Hz, 2H), 2.28 (p**, J=6.1 Hz, 2H). 13C-NMR (100 MHz, CD2Cl2) δ 163.99, 141.21, 128.42, 114.95, 113.90, 65.80, 63.24, 41.91, 32.52 HRMS m/z: calculated for C10H12ClNO4 [M+H]+, 246.0528. found, 246.0529.

Workup

  1. concentrationconcentrated with a rotary evaporator
  2. additionThe mixture was diluted with ethyl acetate (75 mL)
  3. washwashed with 30 mL each of saturated sodium bicarbonate solution, water, and brine
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate, which
  5. customwas removed by filtration
  6. concentrationThe filtrate was concentrated
  7. additionThe fractions containing the product
  8. customwere collected
  9. customvolatiles were removed by rotary evaporation
  10. customThe resulting residue was dried overnight

Sources & evidence

ORD record
ord-61cdb172c64743daaaef5f7d0f7b3111
Source dataset
uspto-grants-2016_07
Patent number
US09381253B2

Reaction notes

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