Water → HCID 53738029、化合物

HRID 1081520ノート

反応式

HRID 1081520 の反応式
[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]

参加物

5

反応物 3

HCID 962WaterHCID 54079109N-methyl-12,13-Bis(4-methoxyphenyl)-11-pentadecenoic amideHCID 178419136HCID 178419136、化合物

生成物 1

HCID 53738029HCID 53738029、化合物収率 35.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To the above dimethoxy amide 15 (117 mg, 0.22 mmol) in CH2Cl2 (1 ml) at 0° C. was added, under argon, 1.0 M 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 16 with x=10) (34 mg, 31%), colorless oil, IR υmax (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=7.3 Hz --N--CH2 --), and 6.59-7.09 (8, m, H--Ar) ppm; MS m/e=493 (M+). ##STR23##

後処理

  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)

出典と根拠

ORDレコード
ord-25fec5e4f8c34a1b8717bdb3b749608e
出典データセット
uspto-grants-1996_12
特許番号
US05585405

反応ノート

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