Triethylamine → HCID 22061495, compound

HRID 1829037Notes

Reaction equation

HRID 1829037 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:7](=[O:8])[O:6][CH2:5]2.[CH2:12]([O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1)[C:13]#[CH:14].C(N(CC)CC)C>CN(C=O)C.C(OCC)C.[Cu]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>[O:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH:16]1[O:15][CH2:12][C:13]#[C:14][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:7](=[O:8])[O:6][CH2:5]2

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranHCID 6031445-Bromophthalide

Product 1

HCID 22061495HCID 22061495, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of 5-bromophthalide (2.00 g, 9.39 mmol), tetrahydro-2-(2-propynyloxy)-2H-pyran (5.3 ml, 37.6 mmol), copper(I) iodide (0.645 g, 3.39 mmol), triethylamine (1.90 g, 18.8 mmol) in DMF (20 ml), was added tetrakis(triphenylphosphine)palladium (1.30 g, 1.13 mmol). The mixture was heated at 65° C. under argon for 16 hours, cooled to room temperature and diluted with diethyl ether (250 ml). The filtrate was washed with brine (4×100 ml), dried over anhydrous Na2SO4, and concentrated to give a dark-reddish residue. Purification of the residue mixture by silica gel column chromatography, eluted with a gradient of EtOAc, led to 5-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-3H-isobenzofuran-1-one as a white solid (2.23 g, 87%).

Workup

  1. temperaturecooled to room temperature
  2. washThe filtrate was washed with brine (4×100 ml)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customto give a dark-reddish residue
  6. customPurification of the residue mixture by silica gel column chromatography
  7. washeluted with a gradient of EtOAc

Sources & evidence

ORD record
ord-57bded8a32ec45f8a063c0a39c4a0f5e
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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