Methanol → methyl 6-methoxy-2,3-dihydro-1H-inden-1-ol

HRID 501696Notes

Reaction equation

HRID 501696 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][CH:4]=1.[BH4-].[Na+].[CH3:15]O>C1COCC1>[CH3:15][C:9]1([OH:12])[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=2)[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3340366-Methoxy-1-IndanoneHCID 4311764Sodium borohydride

Product 1

HCID 68465496methyl 6-methoxy-2,3-dihydro-1H-inden-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Step AA (1): To a solution of 6-methoxy-2,3-dihydro-1H-inden-1-one (24 g) in methanol (150 mL) and THF (50 mL) at 0° C. was added sodium borohydride (5.6 g), and the resulting suspension was stirred at 0° C. for 1 h and rt for 30 min. Solvents were evaporated, and water was added. The aqueous solution was extracted with EtOAc (×4), and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated in vacuo to give methyl 6-methoxy-2,3-dihydro-1H-inden-1-ol as a colorless oil (24.3 g), which was carried forward without purification. 1H NMR (400 MHz, CDCl3): 7.12 (1H, d), 6.95 (1H, d), 6.81 (1H, dd), 5.19 (1H, br. S), 3.79 (3H, s), 2.95 (1H, m), 2.74 (1H, m), 2.50 (1H, m), 1.94 (1H, m).

Workup

  1. customSolvents were evaporated
  2. additionwater was added
  3. extractionThe aqueous solution was extracted with EtOAc (×4)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-0a82c43880c44d63ac245130f0eef859
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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