Tetrahydrofuran → 8-Ethyl-6-trimethylsilanylethynyl-2,2,4,4-tetramethyl chroman

HRID 93977Notes

Reaction equation

HRID 93977 reaction equation
[Br:1][c:2]1[cH:3][c:4]2[c:9]([c:10]([CH2:12][CH3:13])[cH:11]1)[O:8][C:7]([CH3:14])([CH3:15])[CH2:6][C:5]2([CH3:16])[CH3:17].[CH2:24]([N:25]([CH2:26][CH3:27])[CH2:28][CH3:29])[CH3:30].[CH3:18][Si:19]([CH3:20])([CH3:21])[C:22]#[CH:23].[CH3:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].[CH3:85][CH2:86][O:87][C:88](=[O:89])[CH3:90].[Cu:42][I:43].[O:31]1[CH2:32][CH2:33][CH2:34][CH2:35]1.[Pd:44]([Cl:45])[Cl:46].[c:47]1([P:48]([c:49]2[cH:50][cH:51][cH:52][cH:53][cH:54]2)[c:55]2[cH:56][cH:57][cH:58][cH:59][cH:60]2)[cH:61][cH:62][cH:63][cH:64][cH:65]1.[c:66]1([P:67]([c:68]2[cH:69][cH:70][cH:71][cH:72][cH:73]2)[c:74]2[cH:75][cH:76][cH:77][cH:78][cH:79]2)[cH:80][cH:81][cH:82][cH:83][cH:84]1>>[c:2]1([C:23]#[C:22][Si:19]([CH3:18])([CH3:20])[CH3:21])[cH:3][c:4]2[c:9]([c:10]([CH2:12][CH3:13])[cH:11]1)[O:8][C:7]([CH3:14])([CH3:15])[CH2:6][C:5]2([CH3:16])[CH3:17]

Participants

10

Reactant 9

HCID 8028TetrahydrofuranHCID 8058HexaneHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 66111TrimethylsilylacetyleneHCID 695485316-Bromo-8-ethyl-2,2,4,4-tetramethyl chroman

Product 1

HCID 695486138-Ethyl-6-trimethylsilanylethynyl-2,2,4,4-tetramethyl chroman

Sources & evidence

ORD record
ord-a53d5857e32a4b91b8a48145d68bfa3a
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (2/10)

Reaction notes

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