Water → HCID 53704459、化合物

HRID 357325ノート

反応式

HRID 357325 の反応式
[CH2:1]([N:5]([CH3:38])[C:6](=[O:37])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[C:17]([C:29]1[CH:34]=[CH:33][C:32]([O:35]C)=[CH:31][CH:30]=1)[CH:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=1)[CH2:19][CH3:20])[CH2:2][CH2:3][CH3:4].[Br-].[Br-].[Br-].B.O>C(Cl)Cl>[CH2:1]([N:5]([CH3:38])[C:6](=[O:37])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)=[C:18]([C:21]1[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=1)[CH2:19][CH3:20])[CH2:2][CH2:3][CH3:4]

参加物

5

反応物 3

HCID 962WaterHCID 54103883HCID 54103883、化合物HCID 178419136HCID 178419136、化合物

生成物 1

HCID 53704459HCID 53704459、化合物収率 31.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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 (3×). 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, under 0.063 mm, 30 g). Elution with 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 γmax (log ε)=235 (4.25) nm; 1H-NMR (δ, CDCl3), 0.76 (3H, t, J=7.3 Hz, --C2CHH3), 0.96 (3H, t, J=7.3 Hz, N(CH2)3 CH3), 2.05-2.20 (4H, m, CH2 --C=C--C2 --), 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 (8H, m, H--Ar) ppm; MS m/e=493 (M+). ##STR74##

後処理

  1. extractionextracted with ether (3×)
  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, under 0.063 mm, 30 g)
  6. washElution
  7. additionwith mixture of hexane-ethyl acetate (4:1 v/v)

出典と根拠

ORDレコード
ord-bd9e55800b2347fe8bea0b58d1fa2c3c
出典データセット
uspto-grants-1998_11
特許番号
US05840735

反応ノート

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