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Sodium Carbonate → 3-Phenylcyclopentan-1-one

HRID 253089
Notes
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Reaction equation

HRID 253089 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]1(=[O:15])[CH2:14][CH2:13][CH:12]=[CH:11]1.C([O-])([O-])=O.[Na+].[Na+]>O>[C:1]1([CH:12]2[CH2:13][CH2:14][C:10](=[O:15])[CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 135882-Cyclopenten-1-oneHCID 66827Phenylboronic Acid

Product 1

HCID 111374333-Phenylcyclopentan-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of phenylboronic acid (1.63 g, 13.4 mmol), cyclopent-2-enone (1.0 g, 10.4 mmol), and Na2CO3 (2.2 g, 20.8 mmol) was purged with nitrogen for 15 min followed by the addition of [Rh(cod)Cl]2 (100 mg, 0.21 mmol) and water (30 mL). The resulting suspension was heated to 80° C. for 20 min. The mixture was extracted with CH2Cl2, washed with brine, dried over MgSO4 and chromatographed on silica gel using 3:1 hexanes:ethylacetate to afford the title compound as a colorless oil. MS m/z: 161 (M+1).

Workup

  1. customwas purged with nitrogen for 15 min
  2. extractionThe mixture was extracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customchromatographed on silica gel using 3:1 hexanes

Sources & evidence

ORD record
ord-d4d37d3a174f460cbf2bfd8424bc33ef
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07872009B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes