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Ammonium Chloride → 1-Benzyl 6-methyl 3-methoxycarbonyl-4-methoxycarbonylmethyladipate

HRID 263685
ノート
印刷プレビュー

反応式

HRID 263685 の反応式
[CH3:1][O:2][C:3]([CH2:5][CH:6]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH2:7][C:8]([O:10][CH3:11])=[O:9])=[O:4].C1CCCCC1.C([N-]C(C)C)(C)C.[Li+].Br[CH2:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34].[Cl-].[NH4+]>O1CCCC1.CN(C)P(N(C)C)(N(C)C)=O>[CH3:16][O:15][C:13]([CH:12]([CH:6]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH2:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])=[O:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 62576Benzyl bromoacetateHCID 19038603Dimethyl 3-(2-methoxy-2-oxoethyl)pentanedioateHCID 86604122LDA cyclohexane

生成物 1

HCID 190386301-Benzyl 6-methyl 3-methoxycarbonyl-4-methoxycarbonylmethyladipate収率 56.5%

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
2 回
HCID 12679Hexamethylphosphoramide溶媒

実験手順

To 5 ml of a tetrahydrofuran solution containing 600 mg of dimethyl 3-methoxycarbonylmethylglutarate, 1.36 ml of a 1.5M lithium diisopropylamide cyclohexane solution and 0.54 ml of hexamethylphosphoramide were dropwise added at -78° C. under a nitrogen atmosphere, followed by stirring at the same temperature for 1.5 hours. Then, a tetrahydrofuran solution containing 620 mg of benzyl bromoacetate was added thereto, followed by further stirring for one hour. The reaction solution was warmed to room temperature over a period of one hour and then stirred at the same temperature for 2 hours. A saturated ammonium chloride aqueous solution was added to the reaction solution, and the mixture was extracted with ethyl ether. Then, the organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by medium pressure liquid column chromatography (hexane/ethyl acetate=3/1) to obtain 555 mg of the above-identified compound as colorless oily substance.

後処理

  1. additionwere dropwise added at -78° C. under a nitrogen atmosphere
  2. additionwas added
  3. stirringby further stirring for one hour
  4. stirringstirred at the same temperature for 2 hours
  5. extractionthe mixture was extracted with ethyl ether
  6. washThen, the organic layer was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe drying agent was filtered off
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by medium pressure liquid column chromatography (hexane/ethyl acetate=3/1)

出典と根拠

ORDレコード
ord-aa9cce1ce1a54fa384b07c37f8135d2f
出典データセット
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05643958

反応ノート

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