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

HRID 2052323
ノート
印刷プレビュー

反応式

HRID 2052323 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
参加物反応条件実験手順後処理出典と根拠反応ノート

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-a13af1af2abe4b3386cb0199a926b3d5
出典データセット
uspto-grants-1980_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04183870

反応ノート

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