Sodium Carbonate → 2,3-bis((9Z,12Z)-octadeca-9,12-dienyloxy)propanal

HRID 1259006ノート

反応式

HRID 1259006 の反応式
[CH2:1]([O:19][CH:20]([CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:21][OH:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH2:1]([O:19][CH:20]([CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:21]=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 58264329HCID 58264329、化合物HCID 178418287HCID 178418287、化合物

生成物 1

HCID 866675312,3-bis((9Z,12Z)-octadeca-9,12-dienyloxy)propanal収率 39%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2,3-bis((9Z,12Z)-octadeca-9,12-dienyloxy)propan-1-ol (4.0 g, 7.0 mmol) and PCC (4.5 g, 21.0 mmol) in dichloromethane (75 mL) was added sodium carbonate (375 mg, 3.5 mmol). The solution was stirred for 6 hours at room temperature then filtered through silica with diethyl ether rinses (250 mL). The filtrate was concentrated in vacuo to dryness and purified by column chromatography on silica gel 60 (eluted with a gradient of 100% hexanes to 5% ether in hexanes) to afford 2,3-bis((9Z,12Z)-octadeca-9,12-dienyloxy)propanal as a colorless oil (1.6 g, 39%)

後処理

  1. filtrationthen filtered through silica with diethyl ether rinses (250 mL)
  2. concentrationThe filtrate was concentrated in vacuo to dryness
  3. custompurified by column chromatography on silica gel 60 (
  4. washeluted with a gradient of 100% hexanes to 5% ether in hexanes)

出典と根拠

ORDレコード
ord-947886f728cf4cb39c665b350d7484b6
出典データセット
uspto-grants-2013_06
特許番号
US08466122B2

反応ノート

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