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Sodium borohydride → Methyl 2-hydroxy-4-[3-hydroxy-3-(5,6,7,8-tetrahydro-5,6,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate

HRID 861766
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 861766
[OH:1][C:2]1[CH:11]=[C:10]([C:12]#[C:13][C:14](=[O:29])[C:15]2[CH:24]=[CH:23][C:22]3[C:21](C)([CH3:25])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=3[CH:16]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CO.[CH2:32]1COCC1.[BH4-].[Na+]>O>[OH:1][C:2]1[CH:11]=[C:10]([C:12]#[C:13][CH:14]([OH:29])[C:15]2[CH:24]=[CH:23][C:22]3[CH:21]([CH3:25])[CH:20]([CH3:32])[CH2:19][C:18]([CH3:27])([CH3:28])[C:17]=3[CH:16]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]
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Komponenten

5

Edukt 3

HCID 4311764Sodium borohydrideHCID 15285826Methyl 2-hydroxy-4-[3-oxo-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoateHCID 21899815MeOH tetrahydrofuran

Produkt 1

HCID 19700225Methyl 2-hydroxy-4-[3-hydroxy-3-(5,6,7,8-tetrahydro-5,6,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

2.9 g (7.4 mmol) of methyl 2-hydroxy-4-[3-oxo-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate and 100 ml of a methanol/THF (50/50) mixture were introduced into a round-bottomed flask and 140 mg (3.7 mmol) of sodium borohydride were added in small amounts. The reaction mixture was stirred at room temperature for 2 hours, poured into water and extracted with ethyl ether. The organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with a mixture of dichloromethane and hexane (50/50). After evaporation of the solvents, 1.6 g (55%) of the expected compound, with a melting point of 92°-93° C., was recovered.

Aufarbeitung

  1. extractionextracted with ethyl ether
  2. customThe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customwas purified by chromatography on a silica column
  7. washeluted with a mixture of dichloromethane and hexane (50/50)
  8. customAfter evaporation of the solvents, 1.6 g (55%) of the expected compound
  9. customwith a melting point of 92°-93° C., was recovered

Quellen und Nachweise

ORD-Eintrag
ord-5a53f3391e9d426ab9ebd166208c1048
Quelldatensatz
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05716624

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