Acetic Acid → HCID 21914311, compound

HRID 2421355Notes

Reaction equation

HRID 2421355 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH:12]([CH3:14])[CH3:13])=[C:6]([CH:9]=1)[CH:7]=O.[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH:12]([CH3:14])[CH3:13])=[C:6]([CH:9]=1)[CH2:7][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 9750405-bromo-2-isobutoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 21914311HCID 21914311, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 5-bromo-2-isobutoxybenzaldehyde (2.46 g) in 1,2-dichloroethane (40 ml) was added morpholine (0.96 ml) and acetic acid (0.57 ml). The mixture was stirred for 30 minutes before the addition of sodium triacetoxyborohydride (3.04 g). The resulting mixture was stirred at room temperature for 3 h. The reaction was quenched with saturated sodium bicarbonate (30 ml) and stirred for 30 minutes before extraction with ethyl acetate. The organic extracts were dried (MgSO4) and evaporated to give an oil, which was purified by column chromatography eluting with ethyl acetate/iso-hexane (20:80) to give 4-(5-bromo-2-isobutoxybenzyl)morpholine (2.88 g) as an oil.

Workup

  1. customThe reaction was quenched with saturated sodium bicarbonate (30 ml)
  2. stirringstirred for 30 minutes before extraction with ethyl acetate
  3. dry with materialThe organic extracts were dried (MgSO4)
  4. customevaporated
  5. customto give an oil, which
  6. customwas purified by column chromatography
  7. washeluting with ethyl acetate/iso-hexane (20:80)

Sources & evidence

ORD record
ord-d571084e45074b388e08093dc74237d9
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

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