Ammonium Chloride → 1-Cyclopropyl-5-fluoroindan-1-ol

HRID 13691

Reaction equation

HRID 13691 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[CH:12]1([Mg]Br)[CH2:14][CH2:13]1.[Cl-].[NH4+]>CCOCC>[CH:12]1([C:7]2([OH:11])[C:8]3[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)[CH2:5][CH2:6]2)[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 1365375-Fluoro-1-indanoneHCID 178418630HCID 178418630, compound

Product 1

HCID 532567411-Cyclopropyl-5-fluoroindan-1-olYield 106.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 5-fluoroindanone (0.95 g, 6.33 mmol) in anhydrous ether (30 ml) under nitrogen at room temperature add cyclopropyl magnesium bromide (9.1 ml, 7.28 mmol, 1.15 equivalents, 0.80 M in tetrahydrofuran) dropwise while maintaining a gentle reflux. After stirring overnight, quench the reaction at room temperature via dropwise addition of 10% aqueous ammonium chloride. Dilute the reaction with ether, wash with water (2×), dry over anhydrous sodium sulfate, filter, and concentrate to give the title compound (1.30 g, ˜100%). NMR (CDCl3, 400 MHz): δ 0.26 (m, 1H), 0.36-0.51 (m, 3H), 1.21 (m, 1H), 2.13 (m, 1H), 2.28 (m, 1H), 2.80 (m, 1H), 2.95 (m, 1H), 6.88 (m, 2H), 7.29 (m, 1H).

Workup

  1. temperaturewhile maintaining a gentle reflux
  2. customquench
  3. customthe reaction at room temperature
  4. additionDilute
  5. washwash with water (2×)
  6. dry with materialdry over anhydrous sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-4ef2fe94bb2948ac811caf8262aa1d5e
Source dataset
uspto-grants-2010_06
Patent number
US07728150B2

Linked notes

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