Water → (4-Benzyloxy-3,5-difluoro-phenyl)-acetaldehyde

HRID 62893ノート

反応式

HRID 62893 の反応式
[Cl-].[CH3:2][O:3]C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:34]([O:41][C:42]1[C:49]([F:50])=[CH:48][C:45]([CH:46]=O)=[CH:44][C:43]=1[F:51])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.O>C1COCC1>[CH2:34]([O:41][C:42]1[C:49]([F:50])=[CH:48][C:45]([CH2:46][CH:2]=[O:3])=[CH:44][C:43]=1[F:51])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

参加物

6

反応物 4

HCID 962WaterHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 2733832Lithium HexamethyldisilazideHCID 157140264-(Benzyloxy)-3,5-difluorobenzaldehyde

生成物 1

HCID 59455550(4-Benzyloxy-3,5-difluoro-phenyl)-acetaldehyde収率 20.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

After methoxymethyl triphenyl phosphonium chloride (1.04 g, 3.02 mmol) was dissolved in anhydrous THF (9 mL), LiHMDS 1.0M THF solution (3 mL, 3.02 mmol) was added thereto at 0° C., and the mixture was stirred for 15 minutes. 4-Benzyloxy-3,5-difluoro-benzaldehyde (0.50 g, 2.01 mmol) obtained in Step B of Preparation Example 2 was dissolved in anhydrous THF (6 mL), and the solution was added thereto. The mixture was stirred at room temperature for 3 hours. After the termination of the reaction, the reactant was added with water, and then extracted with EtOAc. The organic layer was separated, dried with MgSO4, concentrated under reduced pressure, and then purified by column chromatography (eluent, EtOAc/Hex=1/5). After the obtained product was dissolved in THF (7.68 mL), 2N HCl (3.84 mL) was added thereto, and the mixture was stirred at 70° C. for 5 hours. After the termination of the reaction, the reactant was concentrated under reduced pressure, added with water, and then extracted with EtOAc. The organic layer was separated, dried with MgSO4, concentrated under reduced pressure, and the purified by column chromatography (eluent, EtOAc/Hex=1/5) to obtain the title compound (0.107 g, 20%).

後処理

  1. additionthe solution was added
  2. stirringThe mixture was stirred at room temperature for 3 hours
  3. customAfter the termination of the reaction
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated under reduced pressure
  8. custompurified by column chromatography (eluent, EtOAc/Hex=1/5)
  9. dissolutionAfter the obtained product was dissolved in THF (7.68 mL)
  10. addition2N HCl (3.84 mL) was added
  11. stirringthe mixture was stirred at 70° C. for 5 hours
  12. customAfter the termination of the reaction
  13. concentrationthe reactant was concentrated under reduced pressure
  14. additionadded with water
  15. extractionextracted with EtOAc
  16. customThe organic layer was separated
  17. dry with materialdried with MgSO4
  18. concentrationconcentrated under reduced pressure
  19. customthe purified by column chromatography (eluent, EtOAc/Hex=1/5)

出典と根拠

ORDレコード
ord-2f8c46a0f79a4bfba186beb02fd029b4
出典データセット
uspto-grants-2016_09
特許番号
US09447044B2

反応ノート

読み込み中…