Dichloromethane → HCID 67277626, Verbindung

HRID 1696695

Reaktionsgleichung

Reaktionsgleichung von HRID 1696695
[BH4-].[Na+].ClCCl.[OH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13][CH:14]([CH3:34])[C:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][Si:24]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])=[CH:19][CH:18]=1)=[O:16].[Cl-].[NH4+]>CO>[OH:16][CH:15]([C:17]1[CH:18]=[CH:19][C:20]([O:23][Si:24]([CH:25]([CH3:27])[CH3:26])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:29])[CH3:30])=[CH:21][CH:22]=1)[CH:14]([S:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[OH:6])[CH3:34]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 672774092-[(2-Hydroxyphenyl)thio]-1-{4-[(triisopropylsilyl)oxy]phenyl}propan-1-one

Produkt 1

HCID 67277626HCID 67277626, VerbindungAusbeute 106,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

With cooling with ice, sodium borohydride (5.5 g, 134 mmol) was added to a dichloromethane (500 mL)/methanol (500 mL) mixed solution of 2-[(2-hydroxyphenyl)thio]-1-{4-[(triisopropylsilyl)oxy]phenyl}propan-1-one (48 g, 112 mmol) obtained in Reference Example 1-2, and stirred for 2 hours with cooling with ice, then restored to room temperature, and further stirred for 40 minutes. Aqueous saturated ammonium chloride solution was added, and stirred for a while, and then the solvent was almost completely evaporated off under reduced pressure. The residue was diluted with ethyl acetate, and extracted with aqueous saturated ammonium chloride solution. The organic layer was dried with sodium sulfate, and concentrated under reduced pressure to obtain a crude product (51.4 g) of the intended compound.

Aufarbeitung

  1. customobtained in Reference Example 1-2
  2. temperaturewith cooling with ice
  3. customrestored to room temperature
  4. stirringfurther stirred for 40 minutes
  5. stirringstirred for a while
  6. customthe solvent was almost completely evaporated off under reduced pressure
  7. additionThe residue was diluted with ethyl acetate
  8. extractionextracted with aqueous saturated ammonium chloride solution
  9. dry with materialThe organic layer was dried with sodium sulfate
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-31c3d690cf844e988d754e0954d94b54
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163770B2

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