Sodium Hydroxide → 9-Trityloxy-nonanoic acid

HRID 467391

反応式

HRID 467391 の反応式
[OH-].[Na+].C[O:4][C:5](=[O:34])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[C:15]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]([OH:34])=[O:4])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 42624366Methyl-9-trityloxy-nonanoate

生成物 1

HCID 426243679-Trityloxy-nonanoic acid収率 93%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Aqueous 0.5 M NaOH (13.2 mL, 6.6 mmol) was added to a stirring solution of 15b (1.41 g, 3.3 mol) in 25 mL of THF. The reaction mixture was stirred for 3 days at room temperature, and then the solvent was removed by rotary evaporation. The purification was carried out by flash column chromatography (gradient 10% EtOAc in hexanes to 100% EtOAc) to obtain 1.28 g (93%) of a pale yellow oil 16b. 1H-NMR (400 MHz, CDCl3, δH ppm): 7.43 (6H, m, p-Ar), 7.28 (6H, m, m-Ar), 7.21 (3H, m, o-Ar), 3.03 (2H, t, 3JH—H=6.6 Hz, HO—CH2), 2.33 (2H, t, 3JH—H=7.5 Hz, CH2CO2), 1.56-1.66 (4H, m, 2CH2), 1.20-1.40 (8H, m, 4CH2). 13C-NMR (100 MHz, CDCl3, δH ppm): 180.26, 144.46, 128.63, 127.64, 126.74, 86.22, 63.55, 34.04, 29.95, 29.24, 29.13, 28.96, 26.15, 24.60. HRMS (EI): m/z calcd 416.2351 (C28H32O3), found 416.2360 [M]+.

後処理

  1. customthe solvent was removed by rotary evaporation
  2. customThe purification

出典と根拠

ORDレコード
ord-92766a858b0d461c8d071f33e7ffe6c0
出典データセット
uspto-grants-2014_01
特許番号
US08623326B2

関連ノート

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