Sodium Carbonate → HCID 178444516、化合物

HRID 370371ノート

反応式

HRID 370371 の反応式
C(Cl)(=O)C(Cl)=O.[CH2:7]([C@H:12]1[CH2:17][CH2:16][C@H:15]([C@H:18]2[CH2:23][CH2:22][C@H:21]([C:24]([OH:26])=[O:25])[CH2:20][CH2:19]2)[CH2:14][CH2:13]1)[CH2:8][CH2:9][CH2:10][CH3:11].[CH2:27]([C:30]1[CH:35]=[CH:34][C:33]([C@H:36]2[CH2:41][CH2:40][C@H:39](O)[CH2:38][CH2:37]2)=[CH:32][CH:31]=1)[CH2:28][CH3:29].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.N1C=CC=CC=1.CN(C)C=O>[CH2:27]([C:30]1[CH:31]=[CH:32][C:33]([C@H:36]2[CH2:41][CH2:40][C@H:39]([O:25][C:24]([C@H:21]3[CH2:20][CH2:19][C@H:18]([C@H:15]4[CH2:16][CH2:17][C@H:12]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:13][CH2:14]4)[CH2:23][CH2:22]3)=[O:26])[CH2:38][CH2:37]2)=[CH:34][CH:35]=1)[CH2:28][CH3:29]

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 65578Oxalyl chlorideHCID 178439125HCID 178439125、化合物HCID 178444515HCID 178444515、化合物

生成物 1

HCID 178444516HCID 178444516、化合物収率 44.2%

試薬・触媒・溶媒 3

HCID 1049Pyridine溶媒HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒2 回

反応条件

温度
-20 °C

実験手順

A solution of 0.902 ml of dimethylformamide in 20 ml of acetonitrile was placed at -20° C. while gassing with argon in a sulphonation flask fitted with a mechanical stirrer, serum cap, thermometer and dropping funnel and treated within 2 minutes with 0.338 ml of oxalyl chloride. After completion of the addition, the mixture was stirred at -20° C. for a further 20 minutes and then 1.0 g of trans-4-(trans-4-pentylcyclohexyl)cyclohexanecarboxylic acid was introduced into the resulting white suspension via a solid substance addition tube. The mixture was subsequently stirred at -20° C. for 30 minutes and then treated dropwise at -20° C. within 10 minutes with a solution of 1.97 g of trans-4-(p-propylphenyl)cyclohexanol and 0.9 ml of pyridine in 20 ml of acetonitrile. The mixture was stirred for a further 15 hours while slowly warming to room temperature, then poured into 200 ml of cold 2N sodium carbonate solution and extracted three times with 200 ml of methylene chloride each time. The organic phases were washed once with 100 ml of 2N sodium carbonate solution and twice with 200 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the residue (2.6 g) on 140 g of silica gel using toluene/hexane (volume ratio 1:1) gave 757 mg (44%) of trans-4-(trans-4-pentylcyclohexyl)cyclohexanecarboxylic acid trans-4-(p-propylphenyl)cyclohexyl ester as colourless crystals. A single recrystallization from acetone yielded analytically-pure product of m.p. (C-S) 63.3° C., phase transition S-N 241.5° C., cl.p. (N-I) 285.5° C.

後処理

  1. customwas placed at -20° C.
  2. customwhile gassing with argon in a sulphonation flask
  3. customfitted with a mechanical stirrer
  4. customserum cap
  5. additionAfter completion of the addition
  6. stirringThe mixture was subsequently stirred at -20° C. for 30 minutes
  7. stirringThe mixture was stirred for a further 15 hours
  8. temperaturewhile slowly warming to room temperature
  9. extractionextracted three times with 200 ml of methylene chloride each time
  10. washThe organic phases were washed once with 100 ml of 2N sodium carbonate solution and twice with 200 ml of water each time
  11. dry with materialdried over magnesium sulphate
  12. concentrationconcentrated

出典と根拠

ORDレコード
ord-67a6f76002d14e738eb5bdcd9dffb553
出典データセット
uspto-grants-1985_07
特許番号
US04526704

反応ノート

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