Hexane → 4-[(8-Cyclopropyl-3 4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-2-fluoro-benzoic acid methyl ester

HRID 215516Notes

Reaction equation

HRID 215516 reaction equation
[CH2:32]([N:33]([CH2:34][CH3:35])[CH2:36][CH3:37])[CH3:38].[CH3:20][O:21][C:22]([c:23]1[c:24]([F:30])[cH:25][c:26]([I:29])[cH:27][cH:28]1)=[O:31].[CH3:39][CH2:40][O:41][C:42](=[O:43])[CH3:44].[CH3:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50].[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:51][I:52].[Pd:53]([Cl:54])[Cl:55].[c:56]1([P:57]([c:58]2[cH:59][cH:60][cH:61][cH:62][cH:63]2)[c:64]2[cH:65][cH:66][cH:67][cH:68][cH:69]2)[cH:70][cH:71][cH:72][cH:73][cH:74]1.[c:75]1([P:76]([c:77]2[cH:78][cH:79][cH:80][cH:81][cH:82]2)[c:83]2[cH:84][cH:85][cH:86][cH:87][cH:88]2)[cH:89][cH:90][cH:91][cH:92][cH:93]1>>[CH:1]1([c:4]2[cH:5][c:6]([C:18]#[C:19][c:26]3[cH:25][c:24]([F:30])[c:23]([C:22]([O:21][CH3:20])=[O:31])[cH:28][cH:27]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

9

Reactant 8

HCID 8058HexaneHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 22568800Methyl 2-fluoro-4-iodobenzoateHCID 225689518-Cyclopropyl-6-ethynyl-3 4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cvclopropane]

Product 1

HCID 695484184-[(8-Cyclopropyl-3 4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-2-fluoro-benzoic acid methyl ester

Sources & evidence

ORD record
ord-6b7dcdc875a14b8aab117e32f0ec718c
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (6/10)

Reaction notes

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