Hydrochloric Acid → HCID 69656064, compound

HRID 1830828Notes

Reaction equation

HRID 1830828 reaction equation
CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.C([O:19][C:20](=O)[C:21]([CH2:36][CH3:37])=[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.Cl>C1COCC1.C(OCC)(=O)C.CO>[CH2:36]([C: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)[CH2:20][OH:19])[CH3:37]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 69656486HCID 69656486, compound

Product 1

HCID 69656064HCID 69656064, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under an atmosphere of nitrogen a 1M solution of DIBAL-H in toluene (10.5 ml, 10.5 mmol) was added dropwise at −70° C. over 20 min. to a stirred solution of 2-ethyl-3-(9H-fluoren-2-yl)-acrylic acid ethyl ester (1.54 g, 5.3 mmol) in dry THF (75 ml) and the mixture stirred for 45 min. Methanol (2 ml) was added, followed by 1N HCl and ethyl acetate. The aqueous phase was separated and further extracted with ethyl acetate. The combined organic phases were washed with water, dried (MgSO4), filtered and concentrated in vacuo yielding 1.3 g of 2-ethyl-3-(9H-fluoren-2-yl)-prop-2-en-1-ol.

Workup

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

Sources & evidence

ORD record
ord-fb43f99e99b045dea1574fdaa2af9ef1
Source dataset
uspto-grants-2006_06
Patent number
US07067530B2

Reaction notes

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