Tetrahydrofuran → HCID 69072328, compound

HRID 1765735Notes

Reaction equation

HRID 1765735 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.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

8

Reactant 4

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

Product 1

HCID 69072328HCID 69072328, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 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(11) (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-de1f1df030ba481fb06a1c31955509ec
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

Loading…