6-(7-Hydroxyheptyl)-1,4-dioxaspiro[4.4]nonane-7-carbaldehyde → 6-(7-Hydroxyheptyl)-7-(4-methyl-3-oxooct-1-enyl)-1,4-dioxaspiro[4,4]nonane

HRID 2052319노트

반응식

HRID 2052319 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.[CH3:20][CH:21]([CH2:44][CH2:45][CH2:46][CH3:47])[C:22]([C:24]1C=CC=CC=1P(=C)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:23]>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:24][C:22](=[O:23])[CH:21]([CH3:20])[CH2:44][CH2:45][CH2:46][CH3:47])[CH2:11][CH2:10][C:5]21[O:9][CH2:8][CH2:7][O:6]2

참가 물질

4

반응물 2

HCID 205428916-(7-Hydroxyheptyl)-1,4-dioxaspiro[4.4]nonane-7-carbaldehydeHCID 867367972-Methylhexanoyl-methylenetriphenylphosphorane

생성물 1

HCID 570760486-(7-Hydroxyheptyl)-7-(4-methyl-3-oxooct-1-enyl)-1,4-dioxaspiro[4,4]nonane수율 101.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 7-formyl-6-(7-hydroxyheptyl)-1,4-dioxaspiro[4,4]nonane (3.88 g.) and 2-methylhexanoyl-methylenetriphenylphosphorane (6.0 g.) in dry tetrahydrofuran (30 ml.) was heated to reflux under nitrogen for 18 hours. The solvent was removed in vacuo and the residue triturated with petroleum ether (b.p. 60°-80° C.), allowed to stand at 0° C., filtered to remove triphenylphosphine oxide and the filtrate evaporated to give 6-(7-hydroxyheptyl)-7-(4-methyl-3-oxooct-1-enyl)-1,4-dioxaspiro[4,4]nonane (5.56 g), νmax 1620 cm-1, 1660 cm-1.

후처리

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 18 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue triturated with petroleum ether (b.p. 60°-80° C.)
  5. customto stand at 0° C.
  6. filtrationfiltered
  7. customto remove triphenylphosphine oxide
  8. customthe filtrate evaporated

출처 및 근거

ORD 기록
ord-32c3c405d3a74bcb8357d2b1f5742763
출처 데이터셋
uspto-grants-1980_01
특허 번호
US04183870

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