Acetaldehyde → HCID 9947152、化合物

HRID 1795582ノート

反応式

HRID 1795582 の反応式
[CH3:1][C:2]1[C:3]([NH:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([O-:22])=[O:21])=[CH:18][CH:17]=2)=[CH:4][C:5]2[C:6]([CH3:14])=[CH:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[CH2:25]1COC[CH2:26]1.[CH:30](=O)C.[BH3-]C#N.[Na+]>C(OCC)(=O)C.O.C(O)(=O)C>[CH2:14]([C:6]1[C:5]2[CH:4]=[C:3]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([C:20]([O:22][CH2:25][CH3:26])=[O:21])=[CH:23][CH:24]=3)[C:2]([CH3:1])=[CH:11][C:10]=2[C:9]([CH3:12])([CH3:13])[CH2:8][CH:7]=1)[CH3:30]

参加物

8

反応物 4

HCID 177AcetaldehydeHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 22218201HCID 22218201、化合物2 回

生成物 1

HCID 9947152HCID 9947152、化合物収率 88%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

General Procedure D To a solution of 4-[(3,5,5,8-Tetramethyl-5,6-dihydronaphthalen-2-yl)amino]benzoate (Compound 15, 0.20 g, 0.58 mmol) and 5 mL of THF was added acetaldehyde (0.30 mL, 5.8 mmol), followed by NaBH3CN (0.10 g, 1.74 mmol) and glacial acetic acid (2 mL). The resulting reaction mixture was stirred at room temperature for 24 h, then treated with water and ethyl acetate. The layers were separated, and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with NaHCO3 1 N, brine, and dried over MgSO4, and filtered. The solvent was removed, and the residue was purified by flash column (hexane:ethyl acetate=4:1) to give 0.19 g (88%) of the title compound as a light yellow solid.

後処理

  1. customThe resulting reaction mixture
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with NaHCO3 1 N, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed
  8. customthe residue was purified by flash column (hexane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-6b1e579f68e94edb9f6923d309b065c4
出典データセット
uspto-grants-2006_04
特許番号
US07026487B2

反応ノート

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