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

HRID 372053노트

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HRID 372053 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-22bd11b5147b4dfd9b227aff926484da
출처 데이터셋
uspto-grants-1978_05
특허 번호
US04088695

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