Benzyl Bromide → 12,12-Difluoro-11-dodecenyl phenylmethyl ether

HRID 1090457ノート

反応式

HRID 1090457 の反応式
[H-].[Na+].[F:3][C:4]([F:17])=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16].[H][H].[C:20]1([CH2:26]Br)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1.C(OCC)C>[C:20]1([CH2:26][O:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=[C:4]([F:17])[F:3])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

7

反応物 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 1181687611-Dodecen-1-ol, 12,12-difluoro-HCID 178418361HCID 178418361、化合物

生成物 1

HCID 1991538212,12-Difluoro-11-dodecenyl phenylmethyl ether収率 37.9%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Under a nitrogen atmosphere a stirred mixture of 0.18 gram (0.0075 mole) of sodium hydride in 25 ml of tetrahydrofuran was cooled in an ice-bath, and 1.5 grams (0.0068 mole) of 12,12-difluoro-11-dodecen-1-ol (prepared in Example 5) was added dropwise. Upon completion of addition and when the evolution of hydrogen ceased, a solution of 1.2 grams (0.0068 mole) of phenylmethyl bromide in 5 ml of tetrahydrofuran was added dropwise. Upon completion of addition, the reaction mixture was stirred at ambient temperature for 18 hours. After this time the reaction mixture was taken up in 150 ml of diethyl ether and was washed with 50 ml of water and then with 50 ml of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was subjected to column chromatography on silica gel. Elution was accomplished using methylene chloride. The appropriate fractions were combined and concentrated under reduced pressure yielding 0.8 gram of 12,12-difluoro-11-dodecenyl phenylmethyl ether. The nmr spectrum was consistent with the proposed structure.

後処理

  1. temperaturewas cooled in an ice-bath
  2. additionUpon completion of addition
  3. washwas washed with 50 ml of water
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  7. washElution
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-cf4a01c464e84b0ca983030b556d7ce5
出典データセット
uspto-grants-1992_01
特許番号
US05081287

反応ノート

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