Hydrochloric Acid → HCID 57702262, compound

HRID 1686178Notes

Reaction equation

HRID 1686178 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][C:16]=1[F:17])[C:13](=[O:18])[CH:12]([CH2:19][CH:20]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:21](OC)=[O:22])[CH2:11]2.Cl>C1COCC1>[F:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][C:16]=1[F:17])[CH:13]([OH:18])[CH:12]([CH2:19][CH:20]([CH2:21][OH:22])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:11]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 57702278HCID 57702278, compound

Product 1

HCID 57702262HCID 57702262, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

877 mg (23.1 mmol) of lithium aluminium hydride are initially introduced in 10 ml of THF, and a solution of 5.0 g (15.4 mmol) of methyl 2-(5,6-difluoro-1-oxoindan-2-ylmethyl)heptanoate in 20 ml of THF is added dropwise with ice-cooling. The cooling is removed, and the batch is left to stir at room temp. for 2 h and subsequently refluxed for 30 min. After hydrolysis using ice-water, the solution is acidified using conc. hydrochloric acid, and the aqueous phase is separated off and extracted three times with MTB ether. The combined organic phases are washed with water and dried over sodium sulfate. The solvent is removed in vacuo, giving 5,6-difluoro-2-(2-hydroxymethylheptyl)indan-1-ol as a colourless oil, which is sufficiently pure for further reaction.

Workup

  1. temperaturecooling
  2. customThe cooling is removed
  3. waitthe batch is left
  4. temperaturesubsequently refluxed for 30 min
  5. customAfter hydrolysis
  6. customthe aqueous phase is separated off
  7. extractionextracted three times with MTB ether
  8. washThe combined organic phases are washed with water
  9. dry with materialdried over sodium sulfate
  10. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-1aa669d155094a9ea2ee4b315a13a0b8
Source dataset
uspto-grants-2012_04
Patent number
US08148551B2

Reaction notes

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