Triethylamine → HCID 58444592, compound

HRID 1509763Notes

Reaction equation

HRID 1509763 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:20][CH:19](Br)[CH:18]([CH2:22][CH2:23][CH3:24])[CH2:17][O:16]2)=[CH:11][C:10]=1[F:25])C1C=CC=CC=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.O.CC(OC)(C)C.[Pd]>[F:25][C:10]1[CH:11]=[C:12]([CH:15]2[CH2:20][CH2:19][CH:18]([CH2:22][CH2:23][CH3:24])[CH2:17][O:16]2)[CH:13]=[CH:14][C:9]=1[OH:8]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 58444579HCID 58444579, compound

Product 1

HCID 58444592HCID 58444592, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 15413tert-Butyl methyl etherSolventHCID 22272177Toluene waterSolvent

Procedure

123.0 g (0.30 mol) of 2-(4-benzyloxy-3-fluorophenyl)-4-bromo-5-propyltetrahydropyran are hydrogenated in toluene/water in the presence of Pd/C (5% of Pd) and 86.0 ml (0.60 mol) of triethylamine. The reaction solution is diluted with MTBE, and the organic phase is separated off. The aqueous phase is extracted with MTBE. The combined organic phases are washed with water and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is used directly for the following reaction.

Workup

  1. customthe organic phase is separated off
  2. extractionThe aqueous phase is extracted with MTBE
  3. washThe combined organic phases are washed with water
  4. customdried
  5. concentrationThe solution is concentrated to dryness
  6. customthe residue is used directly for the following reaction

Sources & evidence

ORD record
ord-609d76306b6f4c51aa02b2d46b205656
Source dataset
uspto-grants-2012_07
Patent number
US08211513B2

Reaction notes

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