Water → 2,2-Dimethyl-6-fluoro-3-(2-hydroxyethyl)-chroman

HRID 1032437Notes

Reaction equation

HRID 1032437 reaction equation
C([O:3][C:4]([CH2:6][CH:7]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:17])[CH:14]=2)[O:9][C:8]1([CH3:19])[CH3:18])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[CH3:18][C:8]1([CH3:19])[CH:7]([CH2:6][CH2:4][OH:3])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:17])[CH:14]=2)[O:9]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 543008663-Ethoxycarbonylmethyl-2,2-dimethyl-6-fluoro-chroman

Product 1

HCID 537581732,2-Dimethyl-6-fluoro-3-(2-hydroxyethyl)-chroman

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 3.4 g (12.7 mmol) of 3-ethoxycarbonylmethyl-2,2-dimethyl-6-fluoro-chroman in 40 ml of absolute diethyl ether is added dropwise within a period of 30 minutes, while cooling with ice, to a suspension of 0.97 g (25.5 mmol) of lithium aluminium hydride in 30 ml of absolute diethyl ether. The reaction mixture is then stirred for 2 hours at room temperature and then carefully decomposed with 1 ml of water, 1 ml of sodium hydroxide solution (15%) and 3 ml of water. The resulting precipitate is filtered off with suction and the filtrate is dried over sodium sulfate and concentrated by evaporation in vacuo, yielding 2.75 g (96% of the theoretical yield) of 2,2-dimethyl-6-fluoro-3-(2-hydroxyethyl)-chroman in the form of a light-yellow oil.

Workup

  1. filtrationThe resulting precipitate is filtered off with suction
  2. dry with materialthe filtrate is dried over sodium sulfate
  3. concentrationconcentrated by evaporation in vacuo
  4. customyielding 2.75 g (96% of the

Sources & evidence

ORD record
ord-c6b4c5f0aa8342faa660cfcd30911f79
Source dataset
uspto-grants-1990_09
Patent number
US04957928

Reaction notes

Loading…