Sodium Chloride → 6-[(2,3-Dihydro-1-benzofuran-6-yl)oxy]-4-methylhex-4-enal

HRID 1414832ノート

反応式

HRID 1414832 の反応式
[O:1]1C(C)(C)[CH:2]1[CH2:3][CH2:4][C:5]([CH3:18])=[CH:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:12]2[CH2:13][CH2:14][O:15][C:11]=2[CH:10]=1.Cl(O)(=O)(=O)=O.[Cl-].[Na+].I([O-])(=O)(=O)=O.[Na+]>O.O1CCCC1>[O:1]=[CH:2][CH2:3][CH2:4][C:5]([CH3:18])=[CH:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:12]2[CH2:13][CH2:14][O:15][C:11]=2[CH:10]=1

参加物

7

反応物 4

HCID 5234Sodium ChlorideHCID 24247Perchloric AcidHCID 23667635Sodium periodateHCID 537513846-[(6,7-Epoxy-3,7-dimethyl-2-octenyl)-oxy]-2,3-dihydrobenzofuran

生成物 1

HCID 537384466-[(2,3-Dihydro-1-benzofuran-6-yl)oxy]-4-methylhex-4-enal

試薬・触媒・溶媒 2

HCID 962Water溶媒4 回HCID 8028Tetrahydrofuran溶媒2 回

実験手順

4.64 g. of 6-[(6,7-epoxy-3,7-dimethyl-2,6-nonadienyl)-oxy]-2,3-dihydrobenzofuran (see Example 3) are dissolved in 14 ml. of tetrahydrofuran, diluted with 7.5 ml. of water and treated with a mixture of 0.1 ml. of 70% by weight perchloric acid in 1 ml. of water. The mixture is stirred at room temperature for 4 hours, 10 ml. of saturated aqueous sodium chloride solution are added thereto and the resulting mixture is extracted three times with diethyl ether methylene chloride (9:1 parts by volume). The extracts are washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated. The thus-obtained crude diol is dissolved in 30 ml. of tetrahydrofuran and treated, with ice cooling and under a nitrogen atmosphere, with a solution of 3.2 g. of sodium metaperiodate in 35 ml. of water following which the mixture is stirred overnight at room temperature. For working up, 100 ml. of water are added to the mixture which is then extracted three times with diethyl ether. The extracts are washed with 10% by weight aqueous potassium bicarbonate solution and with semi-saturated and saturated sodium chloride solution, dried over sodium sulfate and evaporated. By chromatography on silica gel with hexane/ethyl acetate (19:1 parts by volume) there is obtained pure 6-[(6-oxo-3-methyl-2-hexenyl)-oxy]-2,3-dihydrobenzofuran which is distilled in a bulb-tube at 100° C./0.02 mmHg.

後処理

  1. extractionthe resulting mixture is extracted three times with diethyl ether methylene chloride (9:1 parts by volume)
  2. washThe extracts are washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe thus-obtained crude diol
  6. dissolutionis dissolved in 30 ml
  7. extractionis then extracted three times with diethyl ether
  8. washThe extracts are washed with 10% by weight aqueous potassium bicarbonate solution
  9. dry with materialwith semi-saturated and saturated sodium chloride solution, dried over sodium sulfate
  10. customevaporated

出典と根拠

ORDレコード
ord-145bc278718c43dbb47a271bec1d562d
出典データセット
uspto-grants-1977_01
特許番号
US04002647

反応ノート

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