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Water → 2-(3-Bromo-alpha-hydroxybenzyl)-3-methoxymethoxypyridine

HRID 442719
ノート
印刷プレビュー

反応式

HRID 442719 の反応式
Br[C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][CH:5]=[CH:4][N:3]=1.CCCCCC.C([Li])CCC.[Br:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=[O:28].O>C(OCC)C>[Br:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]([C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][CH:5]=[CH:4][N:3]=1)[OH:28]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 765833-BromobenzaldehydeHCID 115865732-Bromo-3-(methoxymethoxy)pyridineHCID 178418244HCID 178418244、化合物

生成物 1

HCID 543301292-(3-Bromo-alpha-hydroxybenzyl)-3-methoxymethoxypyridine

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

To a solution of 2-bromo-3-methoxymethoxypyridine (9.11 g) in diethyl ether (200 mL) was added, at -78° C., a 1.6M n-butyl lithium hexane solution (29 mL). The mixture was stirred for one hour at the same temperature, to which was further added a solution of 3-bromobenzaldehyde (6.0 mL) in diethyl ether (5 mL), and the mixture was stirred for one hour at the same temperature. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The extract was washed with a saturated aqueous saline solution, which was then dried (sodium sulfate) and concentrated. The concentrate was purified by means of a silica gel column (ethyl acetate--hexane) to afford 2-(3-bromo-α-hydroxybenzyl)-3-methoxymethoxypyridine (10.89 g) (compound A-1). Physical properties and spectrum data of the product are shown in Table 1 and Table 2. In substantially the same manner as above, compounds A-2 to A-4, and A-6 to A-7 shown in Table 1 were produced.

後処理

  1. stirringthe mixture was stirred for one hour at the same temperature
  2. extractionwas subjected to extraction with ethyl acetate
  3. washThe extract was washed with a saturated aqueous saline solution, which
  4. dry with materialwas then dried (sodium sulfate)
  5. concentrationconcentrated
  6. customThe concentrate was purified by means of a silica gel column (ethyl acetate--hexane)

出典と根拠

ORDレコード
ord-05be92695d8a431cab5559f35ba4cc47
出典データセット
uspto-grants-1999_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05891895

反応ノート

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