Cesium carbonate → HCID 58230603, compound

HRID 390391Notes

Reaction equation

HRID 390391 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:15]#[C:16][CH3:17])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[Br:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26]Br)=[CH:22][CH:21]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[Br:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][O:1][C:2]2[CH:3]=[CH:4][C:5]([C@@H:8]([C:15]#[C:16][CH3:17])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=2)=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 693351,4-Bis(bromomethyl)benzeneHCID 67087065Ethyl (3S)-3-(4-hydroxyphenyl)hex-4-ynoate

Product 1

HCID 58230603HCID 58230603, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution ethyl (3S)-3-(4-hydroxyphenyl)hex-4-ynoate (0.1 g, 0.43 mmol) and 1,4-bis(bromomethyl)benzene (0.227 g, 0.861 mmol) in DMF (5 mL) is added Cs2CO3 (0.28 g, 0.861 mmol) at 0° C. The reaction mixture is allowed to warm to room temperature over 2 h. The reaction mixture is diluted with water (25 mL) and extracted with EtOAc (3×10 mL). The combined organic layer is washed with water (10 mL×3) and saturated brine solution (10 mL), dried, filtered, and evaporated to dryness. The crude product is purified by silica gel chromatography, eluting with hexane:ethyl acetate (9.0:1.0) to give the title compound (0.1 g, 55.9%). ESI/MS m/z (M+H)+ 415.4.

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. washThe combined organic layer is washed with water (10 mL×3) and saturated brine solution (10 mL)
  3. customdried
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product is purified by silica gel chromatography
  7. washeluting with hexane:ethyl acetate (9.0:1.0)

Sources & evidence

ORD record
ord-9a23a3fa711448ac9776d6e128d70d37
Source dataset
uspto-grants-2013_02
Patent number
US08383642B2

Reaction notes

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