Tetrahydrofuran → HCID 69072328, compound

HRID 1869866Notes

Reaction equation

HRID 1869866 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:11]=1)[O:8][C:7]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:6][C:5]2([CH3:20])[CH3:19].C(N(CC)CC)C.O1CCCC1.[CH3:33][Si:34]([C:37]#[CH:38])([CH3:36])[CH3:35]>CCCCCC.[Cu]I.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.C(OCC)(=O)C>[CH2:15]([C:7]1([CH2:17][CH3:18])[CH2:6][C:5]([CH3:20])([CH3:19])[C:4]2[C:9](=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:11]=[C:2]([C:38]#[C:37][Si:34]([CH3:36])([CH3:35])[CH3:33])[CH:3]=2)[O:8]1)[CH3:16]

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 59856228HCID 59856228, compound2×

Product 1

HCID 69072328HCID 69072328, compoundYield 79%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8058HexaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Following General Procedure D and using 6-bromo-2,2-diethyl-8-isopropyl-4,4-dimethyl chroman (Intermediate 27, 0.89 g, 2.62 mmol), triethyl amine (5 mL), tetrahydrofuran (10 mL), copper(I)iodide (0.050 g, 0.26 mmol), trimethylsilyl acetylene (2.5 mL, 17.6 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.184 g, 0.26 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using hexane to 2% ethyl acetate in hexane as the eluent, the title compound (0.73 g, 79%) was obtained as a brown oil.

Sources & evidence

ORD record
ord-2404aa4be3b34c23b092a317ba330d6a
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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