Tetrahydrofuran → HCID 70024647, compound

HRID 1861379Notes

Reaction equation

HRID 1861379 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH2:12][CH3:13])[CH:11]=1)[O:8][C:7]([CH:24]1[CH:29]([CH:30]([CH3:32])[CH3:31])[CH2:28][CH2:27][CH:26]([CH3:33])[CH2:25]1)([CH:14]1[CH:19]([CH:20]([CH3:22])[CH3:21])[CH2:18][CH2:17][CH:16]([CH3:23])[CH2:15]1)[CH2:6][C:5]2([CH:44]1[CH:49]([CH:50]([CH3:52])[CH3:51])[CH2:48][CH2:47][CH:46]([CH3:53])[CH2:45]1)[CH:34]1[CH:39]([CH:40]([CH3:42])[CH3:41])[CH2:38][CH2:37][CH:36]([CH3:43])[CH2:35]1.[CH3:54][Si:55]([C:58]#[CH:59])([CH3:57])[CH3:56].C(N(CC)CC)C.O1CCCC1>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>[CH2:12]([C:10]1[CH:11]=[C:2]([C:59]#[C:58][Si:55]([CH3:57])([CH3:56])[CH3:54])[CH:3]=[C:4]2[C:9]=1[O:8][C:7]([CH:14]1[CH:19]([CH:20]([CH3:22])[CH3:21])[CH2:18][CH2:17][CH:16]([CH3:23])[CH2:15]1)([CH:24]1[CH:29]([CH:30]([CH3:31])[CH3:32])[CH2:28][CH2:27][CH:26]([CH3:33])[CH2:25]1)[CH2:6][C:5]2([CH:34]1[CH:39]([CH:40]([CH3:42])[CH3:41])[CH2:38][CH2:37][CH:36]([CH3:43])[CH2:35]1)[CH:44]1[CH:49]([CH:50]([CH3:52])[CH3:51])[CH2:48][CH2:47][CH:46]([CH3:53])[CH2:45]1)[CH3:13]

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 70024399HCID 70024399, compound2×

Product 1

HCID 70024647HCID 70024647, compound

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 D and using 6-bromo-8-ethyl-2,2,4,4-tetramenthyl chroman (Intermediate 46, 0.5 g, 1.61 mmol), (trimethylsilyl)acetylene (1.57 g, 16.1 mmol), triethyl amine (8 mL), anhydrous tetrahydrofuran (10 mL), copper(I)iodide (0.025 g, 0.13 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.075 g, 0.11 mmol), followed by flash column chromatography over silica gel (230-400 mesh) using 5% ethyl acetate in hexane as the eluent, the title compound was obtained as an oil (0.137 g, 27%).

Sources & evidence

ORD record
ord-83af80029390442c8de0a194370b58e5
Source dataset
uspto-grants-2003_03
Patent number
US06531599B2

Reaction notes

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