2-Heptanone, 1-(triphenylphosphoranylidene)- → 6-(7-Hydroxyheptyl)-7-(3-oxooct-1-enyl)-1,4-dioxaspiro[4,4]nonane

HRID 372053ノート

反応式

HRID 372053 の反応式
[CH:1]([CH:3]1[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH:4]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=O.[C:20]([CH:27]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>O1CCCC1>[OH:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH:4]1[CH:3]([CH:1]=[CH:27][C:20](=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:11][CH2:10][C:5]21[O:9][CH2:8][CH2:7][O:6]2

参加物

4

反応物 2

HCID 107619442-Heptanone, 1-(triphenylphosphoranylidene)-HCID 205428916-(7-Hydroxyheptyl)-1,4-dioxaspiro[4.4]nonane-7-carbaldehyde

生成物 1

HCID 570975946-(7-Hydroxyheptyl)-7-(3-oxooct-1-enyl)-1,4-dioxaspiro[4,4]nonane収率 92.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A mixture of 7-formyl-6-(7-hydroxyheptyl)-1,4-dioxaspiro[4,4]nonane [6 g; prepared as hereinbefore described in Example 1(iv)] and hexanoylmethylenetriphenylphosphorane (8.5 g.) in dry tetrahydrofuran (50 ml.) was heated to reflux under nitrogen for 16 hours. The solvent was removed in vacuo and the residue triturated with petroleum ether (b.p. 60°-80° C.), cooled to 0° C. for 1 day, filtered to remove triphenylphosphine oxide and the filtrate evaporated. The residue was again triturated with petroleum ether (b.p. 60°-80° C.) to remove further triphenylphosphine oxide, filtered, and evaporated to give 6-(7-hydroxyheptyl)-7-(3-oxooct-1-enyl)-1,4-dioxaspiro[4,4]nonane (7.5 g.), νmax 1620 cm-1, 1660 cm-1.

後処理

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 16 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue triturated with petroleum ether (b.p. 60°-80° C.)
  5. filtrationfiltered
  6. customto remove triphenylphosphine oxide
  7. customthe filtrate evaporated
  8. customThe residue was again triturated with petroleum ether (b.p. 60°-80° C.)
  9. customto remove further triphenylphosphine oxide
  10. filtrationfiltered
  11. customevaporated

出典と根拠

ORDレコード
ord-22bd11b5147b4dfd9b227aff926484da
出典データセット
uspto-grants-1978_05
特許番号
US04088695

反応ノート

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