Diethyl Ether → 2-{4-[(8-Cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-phenyl}-propionic acid methyl ester

HRID 292105Notes

Reaction equation

HRID 292105 reaction equation
[CH2:33]([N:34]([CH2:35][CH3:36])[CH2:37][CH3:38])[CH3:39].[CH3:20][O:21][C:22]([CH:23]([CH3:24])[c:25]1[cH:26][cH:27][c:28]([I:31])[cH:29][cH:30]1)=[O:32].[CH3:40][CH2:41][O:42][CH2:43][CH3:44].[CH:1]1([c:4]2[cH:5][c:6]([C:18]#[CH:19])[cH:7][c:8]3[c:13]2[O:12][C:11]2([CH2:10][C:9]3([CH3:16])[CH3:17])[CH2:14][CH2:15]2)[CH2:2][CH2:3]1.[Cu:45][I:46].[Pd:47]([Cl:48])[Cl:49].[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>>[CH:1]1([c:4]2[cH:5][c:6]([C:18]#[C:19][c:28]3[cH:27][cH:26][c:25]([CH:23]([C:22]([O:21][CH3:20])=[O:32])[CH3:24])[cH:30][cH:29]3)[cH:7][c:8]3[c:13]2[O:12][C:11]2([CH2:10][C:9]3([CH3:16])[CH3:17])[CH2:14][CH2:15]2)[CH2:2][CH2:3]1

Participants

8

Reactant 7

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 10589545Methyl 2-(4-iodophenyl)propanoateHCID 225689518-Cyclopropyl-6-ethynyl-3 4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cvclopropane]

Product 1

HCID 690752312-{4-[(8-Cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-phenyl}-propionic acid methyl ester

Sources & evidence

ORD record
ord-59d352f7843d479ca3c1a87acbea1228
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (8/10)

Reaction notes

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