Tetrahydrofuran → 8-Cyclopropyl-3,4-dihydro-4,4-dimethyl-6-(trimethylsilanyl)ethynylspiro[2 H 1-benzopyran-2,1'-cyclopropane]

HRID 204202Notes

Reaction equation

HRID 204202 reaction equation
[Br:1][c:2]1[cH:3][c:4]([CH:16]2[CH2:17][CH2:18]2)[c:5]2[c:6]([cH:15]1)[C:7]([CH3:13])([CH3:14])[CH2:8][C:9]1([O:10]2)[CH2:11][CH2:12]1.[CH2:25]([N:26]([CH2:27][CH3:28])[CH2:29][CH3:30])[CH3:31].[CH3:19][Si:20]([CH3:21])([CH3:22])[C:23]#[CH:24].[CH3:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].[CH3:86][CH2:87][O:88][C:89](=[O:90])[CH3:91].[Cu:43][I:44].[O:32]1[CH2:33][CH2:34][CH2:35][CH2:36]1.[Pd:45]([Cl:46])[Cl:47].[c:48]1([P:49]([c:50]2[cH:51][cH:52][cH:53][cH:54][cH:55]2)[c:56]2[cH:57][cH:58][cH:59][cH:60][cH:61]2)[cH:62][cH:63][cH:64][cH:65][cH:66]1.[c:67]1([P:68]([c:69]2[cH:70][cH:71][cH:72][cH:73][cH:74]2)[c:75]2[cH:76][cH:77][cH:78][cH:79][cH:80]2)[cH:81][cH:82][cH:83][cH:84][cH:85]1>>[c:2]1([C:24]#[C:23][Si:20]([CH3:19])([CH3:21])[CH3:22])[cH:3][c:4]([CH:16]2[CH2:17][CH2:18]2)[c:5]2[c:6]([cH:15]1)[C:7]([CH3:13])([CH3:14])[CH2:8][C:9]1([O:10]2)[CH2:11][CH2:12]1

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 225689116-Bromo-8-cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]

Product 1

HCID 225688398-Cyclopropyl-3,4-dihydro-4,4-dimethyl-6-(trimethylsilanyl)ethynylspiro[2 H 1-benzopyran-2,1'-cyclopropane]

Sources & evidence

ORD record
ord-ff0fc70ed6d24af48e545043934fe30a
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (6/10)

Reaction notes

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