Propargyl alcohol → HCID 68650633, compound

HRID 646727Notes

Reaction equation

HRID 646727 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.C(N(CC)CC)C.[CH2:19]([OH:22])[C:20]#[CH:21]>CN(C=O)C.[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:22][CH2:19][C:20]#[C:21][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2

Participants

7

Reactant 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 5206955-Bromo-1-indanone

Product 1

HCID 68650633HCID 68650633, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

5-Bromo-2,3-dihydro-1H-inden-1-one (1.68 g, 7.99 mmol) was dissolved in DMF and treated with triethylamine (1.61 g, 15.98 mmol), copper iodide (152 mg, 0.79 mmol) and prop-2-yn-1-ol (2.24 g, 39.96 mmol) in the presence of Pd(PPh3)4 (462 mg, 0.39 mmol) at ambient temperature. After being refluxed for 16 h, the reaction mixture was extracted with ethyl acetate (100 mL×3) and washed with brine. The combined organic layers were dried over MgSO4. Solvent removal under vacuum gave crude tan oil. Purification by preparative thin-layer chromatography afforded 5-(hydroxyprop-1-yn-1-yl)-2,3-dihydro-1H-indene-1-one (1.06 g, 72% yield): 1H NMR (400 MHz, CD3OD): δ 7.63 (d, 1H), 7.59 (s, 1H), 7.42 (d, 1H), 4.45 (s, 2H), 3.18 (m, 2H), 2.69 (m, 2H); MS (EI) for C12H10O2: 187.20 (MH+).

Workup

  1. temperatureAfter being refluxed for 16 h
  2. extractionthe reaction mixture was extracted with ethyl acetate (100 mL×3)
  3. washwashed with brine
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customSolvent removal under vacuum
  6. customgave crude tan oil
  7. customPurification by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-432a5b9640b44d958fb379a359d272e0
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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