Tetrahydrofuran → 2-(1,3-Dioxaindan-5-yl)ethan-1-ol

HRID 747269Notes

Reaction equation

HRID 747269 reaction equation
[CH2:1]1[O:5][C:4]2[CH:6]=[C:7]([CH2:10][C:11](O)=[O:12])[CH:8]=[CH:9][C:3]=2[O:2]1.C1COCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(OCC)C>[O:2]1[C:3]2[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:12])=[CH:6][C:4]=2[O:5][CH2:1]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 9357Potassium Sodium TartrateHCID 76115Benzo-1,3-dioxole-5-acetic acid2×HCID 21226445Aluminium lithium hydride2×

Product 1

HCID 27598462-(1,3-Dioxaindan-5-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  1. customto quench the reaction mixture
  2. extractionThe aqueous layer was extracted with ether (3×100 mL)
  3. dry with materialThe combined organic fractions were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-bc91680931e64c7bb7577bc81841648c
Source dataset
uspto-grants-2008_07
Patent number
US07396849B2

Reaction notes

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