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

HRID 372049ノート

反応式

HRID 372049 の反応式
[CH3:1][CH:2]([CH2:12][CH2:13][CH2:14][CH3:15])[C:3](=[O:11])[CH2:4]P(=O)(OC)OC.[H-].[Na+].[H][H].[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>O1CCCC1.C(O)(=O)C>[OH:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH:23]1[CH:22]([CH:20]=[CH:4][C:3](=[O:11])[CH:2]([CH3:1])[CH2:12][CH2:13][CH2:14][CH3:15])[CH2:30][CH2:29][C:24]21[O:25][CH2:26][CH2:27][O:28]2

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 12906670Dimethyl 2-Oxo-3-methylheptylphosphonateHCID 205428916-(7-Hydroxyheptyl)-1,4-dioxaspiro[4.4]nonane-7-carbaldehydeHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

Dimethyl 3-methyl-2-oxoheptylphosphonate (5.1 g.; prepared as described in the Specification of Netherlands Patent Application No. 7203126) in dry tetrahydrofuran (20 ml.) was added dropwise to a stirred suspension of sodium hydride (0.52 g.) in dry tetrahydrofuran (150 ml.) at ambient temperature under nitrogen. The reaction mixture was stirred at ambient temperature until hydrogen evolution had ceased, and then treated with a solution of 7-formyl-6-(7-hydroxyheptyl)-1,4-dioxaspiro[4,4]nonane (5.1 g.) in dry tetrahydrofuran (50 ml.). After stirring for a further period of 2 hours at ambient temperature the reaction mixture was acidified to pH 4 with glacial acetic acid and then concentrated under reduced pressure. The residue was triturated with diethyl ether and filtered. The filtrate was washed with dilute aqueous sodium carbonate solution and water respectively, then dried over sodium sulphate. Removal of the solvent under reduced pressure gave crude 6-(7-hydroxyheptyl)-7-(4-methyl-3-oxooct-1-enyl)-1,4-dioxaspiro[4,4]nonane (7.6 g.), νmax (liquid film) 3450 cm-1, 1680 cm-1, 1660 cm-1, 1620 cm-1, 1380 cm-1, 1040 cm-1, which was used in the next stage without further purification being necessary.

後処理

  1. customprepared
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was triturated with diethyl ether
  4. filtrationfiltered
  5. washThe filtrate was washed with dilute aqueous sodium carbonate solution and water respectively
  6. dry with materialdried over sodium sulphate
  7. customRemoval of the solvent under reduced pressure

出典と根拠

ORDレコード
ord-c6b3d6d155664e4c97d97badc48d9fb0
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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