Phenylacetylene → 6-(Phenylethynyl)-2',4',5',6'-tetrahydrospiro[chroman-2,3'-pyran]-4-one

HRID 694000Notes

Reaction equation

HRID 694000 reaction equation
[Br:1][c:2]1[cH:3][c:4]2[c:9]([cH:10][cH:11]1)[O:8][C:7]1([CH2:6][C:5]2=[O:17])[CH2:12][O:13][CH2:14][CH2:15][CH2:16]1.[Cu:45][I:46].[Pd:47]([Cl:48])[Cl:49].[c:18]1([P:19]([c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[cH:32][cH:33][cH:34][cH:35][cH:36]1.[c:37]1([C:43]#[CH:44])[cH:38][cH:39][cH:40][cH:41][cH:42]1.[c:50]1([P:51]([c:52]2[cH:53][cH:54][cH:55][cH:56][cH:57]2)[c:58]2[cH:59][cH:60][cH:61][cH:62][cH:63]2)[cH:64][cH:65][cH:66][cH:67][cH:68]1.[c:69]1([P:70]([c:71]2[cH:72][cH:73][cH:74][cH:75][cH:76]2)[c:77]2[cH:78][cH:79][cH:80][cH:81][cH:82]2)[cH:83][cH:84][cH:85][cH:86][cH:87]1>>[c:2]1([C:44]#[C:43][c:37]2[cH:38][cH:39][cH:40][cH:41][cH:42]2)[cH:3][c:4]2[c:9]([cH:10][cH:11]1)[O:8][C:7]1([CH2:6][C:5]2=[O:17])[CH2:12][O:13][CH2:14][CH2:15][CH2:16]1

Participants

6

Reactant 5

HCID 10821PhenylacetyleneHCID 11776Triphenylphosphine3×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 584238236-Bromo-2',4',5',6'-tetrahydrospiro[chroman-2,3'-pyran]-4-one

Product 1

HCID 584246946-(Phenylethynyl)-2',4',5',6'-tetrahydrospiro[chroman-2,3'-pyran]-4-one

Sources & evidence

ORD record
ord-bfb5c4df420d4e18931964b5e04f1d0c
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (3/10)

Reaction notes

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