Tetrahydrofuran → 6-Trimethlsilanylethynyl-2,2,4,4-tetramethyl chroman-8-carbaldehyde

HRID 898673Notes

Reaction equation

HRID 898673 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH:12]=[O:13])[CH:11]=1)[O:8][C:7]([CH3:15])([CH3:14])[CH2:6][C:5]2([CH3:17])[CH3:16].C(N(CC)CC)C.O1CCCC1.[CH3:30][Si:31]([C:34]#[CH:35])([CH3:33])[CH3:32]>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>[CH3:30][Si:31]([C:34]#[C:35][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH:12]=[O:13])[CH:11]=1)[O:8][C:7]([CH3:15])([CH3:14])[CH2:6][C:5]2([CH3:17])[CH3:16])([CH3:33])[CH3:32]

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 225689466-Bromo-2,2,4,4-tetramethyl chroman-8-carbaldehyde

Product 1

HCID 596920816-Trimethlsilanylethynyl-2,2,4,4-tetramethyl chroman-8-carbaldehydeYield 99%

Reagents, catalysts & solvents 4

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

Procedure

Following general procedure I and using 6-bromo-2,2,4,4-tetramethyl chroman-8-carbaldehyde (Compound 42, see U.S. Pat. No. 6,303,785, 1.78 g, 5.4 mmol), triethyl amine (5 mL), tetrahydrofuran (10 mL), copper(I)iodide (0.23 g, 1.2 mmol), trimethylsilyl acetylene (3.3 mL, 23 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.843 g, 1.2 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5% ethyl acetate in hexane as the eluent, the title compound (1.77 g, 99%) was obtained as a pale yellow solid.

Sources & evidence

ORD record
ord-a4c16d5fad3e4c2fbd60ff517b05dc2c
Source dataset
uspto-grants-2008_04
Patent number
US07351737B2

Reaction notes

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