Hexane → [4-(Benzyloxy)-5-bromo-2-methylphenyl][4-[2-(methoxymethoxy)ethyl]phenyl]methanol

HRID 1009872ノート

反応式

HRID 1009872 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH2:11][O:12][CH3:13])=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.[CH2:25]([O:32][C:33]1[C:40]([Br:41])=[CH:39][C:36]([CH:37]=[O:38])=[C:35]([CH3:42])[CH:34]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:25]([O:32][C:33]1[C:40]([Br:41])=[CH:39][C:36]([CH:37]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH2:11][O:12][CH3:13])=[CH:4][CH:3]=2)[OH:38])=[C:35]([CH3:42])[CH:34]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

参加物

7

反応物 5

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 155094031-Bromo-4-[2-(methoxymethoxy)ethyl]benzeneHCID 866384374-(Benzyloxy)-5-bromo-2-methylbenzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 67304665[4-(Benzyloxy)-5-bromo-2-methylphenyl][4-[2-(methoxymethoxy)ethyl]phenyl]methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a tetrahydrofuran solution (1 L) of 1-bromo-4-[2-(methoxymethoxy)ethyl]benzene (50.2 g, 0.205 mol) was added dropwise under nitrogen atmosphere at −78° C. a 2.6 M n-butyllithium solution in hexane (78.8 mL, 0.205 mol), and the mixture was stirred for 15 minutes at the same temperature. Then a tetrahydrofuran solution (150 mL) of 4-benzyloxy-5-bromo-2-methyl benzaldehyde (56.9 g, 0.195 mol) was added dropwise over an hour, and the mixture was stirred for 30 minutes at the same temperature. To the reaction solution was added a saturated aqueous solution of ammonium chloride, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of ammonium chloride and brine, and dried with anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was evaporated under reduced pressure to obtain [4-(benzyloxy)-5-bromo-2-methylphenyl][4-[2-(methoxymethoxy)ethyl]phenyl]methanol.

後処理

  1. stirringthe mixture was stirred for 30 minutes at the same temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of ammonium chloride and brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-7b0c26a023574ec3a3131ea2641a66bf
出典データセット
uspto-grants-2011_07
特許番号
US07973012B2

反応ノート

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