Toluene → HCID 22048458, compound

HRID 1830825Notes

Reaction equation

HRID 1830825 reaction equation
CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.C([O:19][C:20](=O)/[CH:21]=[CH:22]/[C:23]1[CH:35]=[CH:34][C:33]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26][C:25]=2[CH:24]=1)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].[OH-].[Na+]>C1COCC1.CO>[CH:24]1[C:25]2[CH2:26][C:27]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:33]=2[CH:34]=[CH:35][C:23]=1/[CH:22]=[CH:21]/[CH2:20][OH:19]

Participants

8

Reactant 5

HCID 1140TolueneHCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 14798Sodium HydroxideHCID 69655863HCID 69655863, compound

Product 1

HCID 22048458HCID 22048458, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an atmosphere of nitrogen a 1M solution of DIBAL-H in toluene (80 ml, 80 mmol) was added dropwise at −70° C. over 20 min. to a stirred solution of (E)-3-(9H-fluoren-2-yl)-acrylic acid ethyl ester (5.3 g, 20.0 mmol) in dry THF (150 ml) and the mixture stirred for 30 min. Methanol (2 ml) was added, followed by saturated aqueous Rochelle's salt (100 ml), and 1N NaOH. The aqueous phase was separated and further extracted with dichloromethane. The combined organic phases were washed with water (300 mL), dried (MgSO4), filtered and concentrated in vacuo yielding 4.1 g (92%) of (E)-3-(9H-fluoren-2-yl)-prop-2-en-1-ol.

Workup

  1. customThe aqueous phase was separated
  2. extractionfurther extracted with dichloromethane
  3. washThe combined organic phases were washed with water (300 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5653bf36c9204b2e8cd1462e8779a7e6
Source dataset
uspto-grants-2006_06
Patent number
US07067530B2

Reaction notes

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