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Hydrochloric Acid → 3-Chloro-6-cyclopentyl-6-[4-(3-hydroxy-phenyl)-but-3-ynyl]-dihydro-pyran-2,4-dione

HRID 1453328
Notes
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Reaction equation

HRID 1453328 reaction equation
[CH2:1]([C:5]1([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[O:10][C:9](=[O:11])[CH:8]([Cl:12])[C:7](=[O:13])[CH2:6]1)[CH2:2][C:3]#[CH:4].I[C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1.Cl>CN(C=O)C.C(NC(C)C)(C)C.C(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:12][CH:8]1[C:7](=[O:13])[CH2:6][C:5]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)([CH2:1][CH2:2][C:3]#[C:4][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=2)[O:10][C:9]1=[O:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 3

HCID 313Hydrochloric AcidHCID 122723-IodophenolHCID 224997916-But-3-ynyl-3-chloro-6-cyclopentyl-dihydro-pyran-2,4-dione

Product 1

HCID 587622273-Chloro-6-cyclopentyl-6-[4-(3-hydroxy-phenyl)-but-3-ynyl]-dihydro-pyran-2,4-dione

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 6228DimethylformamideSolvent
HCID 6344DichloromethaneSolvent
HCID 7912DiisopropylamineSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 6-but-3-ynyl-3-chloro-6-cyclopentyl-dihydro-pyran-2,4-dione (200 mg, 0.66 mmol) from Step 4 above, 3-iodophenol (145 mg, 0.66 mmol), bis(triphenylphosphine)palladium (II) dichloride (18 mg, 0.026 mmol), and copper (I) iodide (10 mg, 0.052 mmol) in DMF (0.66 mL) and diisopropylamine (0.66 mL) was sonicated for 1 minute and then heated to 90° C. for 20 minutes. The reaction was cooled to room temperature, and then diluted with 10 mL CH2Cl2 The reaction was then neutralized to a pH of 4 with 6 N HCl and the layers were separated. The aqueous layer was extracted with 3×10 mL CH2Cl2 and the organic layers were combined, and then dried over sodium sulfate. After filtering the solids, the organic layer was concentrated to a dark oil, which was used without further purification. MS (ESI): 359 (M−H), 361 (M+2−H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with 3×10 mL CH2Cl2
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtering the solids
  6. concentrationthe organic layer was concentrated to a dark oil, which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-6f83910178fe4c869d813fa15c162d47
Source dataset
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07473790B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes