Acetic Acid → 6-(7-Hydroxyheptyl)-7-(3-oxo-5-phenylpent-1-enyl)-1,4-dioxaspiro[4,4] nonane

HRID 2286078노트

반응식

HRID 2286078 반응식
[O:1]=[C:2]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3]P(=O)(OC)OC.[H-].[Na+].[CH:20]([CH:22]1[CH2:30][CH2:29][C:24]2([O:28][CH2:27][CH2:26][O:25]2)[CH:23]1[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][OH:38])=O.C(O)(=O)C>O1CCCC1>[OH:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH:23]1[CH:22]([CH:20]=[CH:3][C:2](=[O:1])[CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:30][CH2:29][C:24]21[O:25][CH2:26][CH2:27][O:28]2

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 2733973Dimethyl(2-oxo-4-phenylbutyl)phosphonateHCID 205428916-(7-Hydroxyheptyl)-1,4-dioxaspiro[4.4]nonane-7-carbaldehyde

생성물 1

HCID 570149746-(7-Hydroxyheptyl)-7-(3-oxo-5-phenylpent-1-enyl)-1,4-dioxaspiro[4,4] nonane수율 99.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

A solution of dimethyl 2-oxo-4-phenylbutylphosphonate [2.5 g; prepared as described hereinafter in Example 9(iv)] in anhydrous tetrahydrofuran (50 ml.) was added to a stirred suspension of sodium hydride (0.24 g.) in tetrahydrofuran (20 ml.). The mixture was stirred at room temperature in an atmosphere of nitrogen for 24 hours, then treated dropwise with a solution of 7-formyl-6-(7-hydroxyheptyl)-1,4-dioxaspiro[4,4]nonane [2.7 g; prepared as described hereinbefore in Example 1(iv)] in tetrahydrofuran (30 ml.) and stirred for a further 2 hours in an atmosphere of nitrogen. The mixture was acidified to pH 4 by the addition of glacial acetic acid, the solvents were removed in vacuo and the residue was extracted with diethyl ether. The ethereal solution was washed with aqueous sodium bicarbonate solution (10% w/v) and then with water and dried over anhydrous magnesium sulphate. Evaporation of the solution gave 6-(7-hydroxyheptyl)-7-(3-oxo-5-phenylpent-1-enyl)-1,4-dioxaspiro[ 4,4]nonane (3.9 g.), in the form of a yellow oil (νmax 955 cm-1, 990 cm-1, 1625 cm-1, 1665 cm-1, 1690 cm-1).

후처리

  1. stirringstirred for a further 2 hours in an atmosphere of nitrogen
  2. customthe solvents were removed in vacuo
  3. extractionthe residue was extracted with diethyl ether
  4. washThe ethereal solution was washed with aqueous sodium bicarbonate solution (10% w/v)
  5. dry with materialwith water and dried over anhydrous magnesium sulphate
  6. customEvaporation of the solution

출처 및 근거

ORD 기록
ord-13964e7edbcf4939878d8dbc35ef2357
출처 데이터셋
uspto-grants-1982_04
특허 번호
US04325967

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