Hydrochloric Acid → HCID 59288344, compound

HRID 2420637Notes

Reaction equation

HRID 2420637 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH:12]([C:18](OCC)=[O:19])[C:13](OCC)=[O:14])[O:8][CH2:7][CH:6]([CH2:23][CH2:24][CH3:25])[CH2:5]2.[H-].C([Al+]CC(C)C)C(C)C.Cl>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH:12]([CH2:18][OH:19])[CH2:13][OH:14])[O:8][CH2:7][CH:6]([CH2:23][CH2:24][CH3:25])[CH2:5]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 59288369HCID 59288369, compound

Product 1

HCID 59288344HCID 59288344, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

8.7 g (21.1 mmol) of the diethyl 2-(6-fluoro-3-propylchroman-7-yl)malonate obtained under 1.2. are initially introduced in 60 ml of toluene, and 106 ml (106 mmol) of a 1 M solution of diisobutylaluminium hydride in toluene are added dropwise at 5° C. The batch is subsequently added to ice-cold sat. ammonium chloride soln., acidified using dil. hydrochloric acid and extracted with MTB ether. The combined org. phases are dried over sodium sulfate and evaporated. Chromatography of the crude product on silica gel with MTB ether/heptane (4:1) gives 2-(6-fluoro-3-propylchroman-7-yl)propane-1,3-diol as a colourless solid.

Workup

  1. additionThe batch is subsequently added to ice-cold sat. ammonium chloride soln
  2. extractionextracted with MTB ether
  3. dry with materialphases are dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-eb90ce9974ac4472a69af2a9bfcbb89c
Source dataset
uspto-grants-2011_06
Patent number
US07955664B2

Reaction notes

Loading…