Reaktion #834451

ord-bc91680931e64c7bb7577bc81841648c

Reaktionsgleichung

O=C(O)Cc1ccc2c(c1)OCO2
3,4-(methylenedioxy)phenylacetic acid
O=C(O)Cc1ccc2c(c1)OCO2
Intermediate D1
O=C(O)Cc1ccc2c(c1)OCO2
3,4-(methylenedioxy)phenylacetic acid
C1CCOC1
THF
[Al+3].[H-].[H-].[H-].[H-].[Li+]
lithium aluminum hydride
O=C([O-])[C@H](O)[C@@H](O)C(=O)[O-].[K+].[Na+]
Rochelle's salt
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
OCCc1ccc2c(c1)OCO2
2-benzo[1,3]dioxol-5-yl-ethanol

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeto quench the reaction mixture
  2. 2
    ExtraktionThe aqueous layer was extracted with ether (3×100 mL)
  3. 3
    TrocknenThe combined organic fractions were dried over MgSO4
  4. 4
    Filtrationfiltered
  5. 5
    Sonstigeevaporated

Vorschrift

A solution of 3,4-(methylenedioxy)phenylacetic acid (Intermediate D1) (commercially available from Aldrich) (2 g, 11 mmol) in diethyl ether (40 mL) and THF (60 mL) was treated with lithium aluminum hydride: LiAlH4 (24 mL, 1 M in ether) at rt for 16 h. Rochelle's salt solution was added to quench the reaction mixture. The aqueous layer was extracted with ether (3×100 mL). The combined organic fractions were dried over MgSO4, filtered and evaporated to give 1.8 g of 2-benzo[1,3]dioxol-5-yl-ethanol (Intermediate D2) that was sufficiently pure to be used in the next synthetic step.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07396849B2uspto-grants-2008_07