Water → HCID 53738029, compound

HRID 275531Notes

Reaction equation

HRID 275531 reaction equation
[CH3:1][NH:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[C:14]([C:26]1[CH:31]=[CH:30][C:29]([O:32]C)=[CH:28][CH:27]=1)[CH:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=1)[CH2:16][CH3:17].[Br-].[Br-].[Br-].B.O>C(Cl)Cl>[CH3:1][NH:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)=[C:15]([C:18]1[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=1)[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 54079109HCID 54079109, compoundHCID 178419136HCID 178419136, compound

Product 1

HCID 53738029HCID 53738029, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the above dimethoxy amide 4 (117 mg, 0.22 mmol) in CH2Cl2 (1 ml) at 0° C. was added, under argon, 1.0M borane tribromide (675 μl). The solution was stirred for 1 hour, then poured into water and extracted with ether (3x). The organic solution was washed with water, dried on magnesium sulfate, and evaporated to dryness. The residue was purified by "Flash chromatography" on silica gel (Kieselgel 60, Merck, unter 0.063 mm, 30 g). Elution with a mixture of hexane-ethyl acetate (4:1 v/v) gave N-butyl, N-methyl-12,13-Bis (4-hydroxyphenyl)-12-pentadecenoic amide (EM-142, compound 5 with x=10) (34 mg, 31%), colorless oil, IR νmax (neat) 3300, 1600 cm-1 ; UV λmax (log ε)=235 (4.25) nm; 1H-NMR (δ, CDCl3), 0.76 (3H, t, J=7.3 Hz, --CH2CH3), 0.96 (3H, t, J=7.3 Hz, N (CH2)3CH3), 2,05-2.20 (4H, m, CH2 --C=C--CH2 --), 2.35 (2H, t,J=7.0 Hz, --CH2CON--), 2.97 and 3.00 (3H, s, --NCH3), 3.29 and 3.41 (2H, 2t, J=7.3Hz, --N--CH2 --), and 6.59-7.09 (8H, m, H-Ar) ppm; MS m/e=493 (M+). ##STR13##

Workup

  1. extractionextracted with ether (3x)
  2. washThe organic solution was washed with water
  3. customdried on magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by "Flash chromatography" on silica gel (Kieselgel 60, Merck, unter 0.063 mm, 30 g)
  6. washElution
  7. additionwith a mixture of hexane-ethyl acetate (4:1 v/v)

Sources & evidence

ORD record
ord-994d5ec1a859413ab096343d5acd0dfc
Source dataset
uspto-grants-1995_02
Patent number
US05393785

Reaction notes

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