Tributylphenyltin → HCID 20090655, compound

HRID 275186Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:23]([CH3:28])([CH3:27])[CH2:22][CH2:21][C:20]([CH3:30])([CH3:29])[C:19]=2[CH:18]=1)[CH:10]=[O:11])(=O)=O.[C:33]1([Sn](CCCC)(CCCC)CCCC)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH3:28][C:23]1([CH3:27])[CH2:22][CH2:21][C:20]([CH3:29])([CH3:30])[C:19]2[CH:18]=[C:17]([CH2:16][O:15][C:14]3[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=3[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:26]=[CH:25][C:24]1=2

Participants

Reactant 2

HCID 607632Tributylphenyltin

HCID 20090665HCID 20090665, compound

Product 1

HCID 20090655HCID 20090655, compoundYield 65%

Procedure

3-Trifluoromethylsulphonyloxy-4-[5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl]methoxy benzaldehyde (42) (0.745 g., 1.58 mmol) is coupled with phenyltributylstannane (0.870 g., 2.38 mmol) via the method of Example 3 to afford 2-[5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl]methoxy-[1,1'-biphenyl]-5-carboxaldehyde (43) (0.404 g., 1.02 mmol, 65%): chromatographed on silica gel using CH2Cl2 /hexane; 1H NMR (300 MHz, CDCl3) δ 9.93 (s, 1H, CHO), 7.87 (d, J =2 Hz, 1H, ArH), 7.84 (dd, J=2, 8 Hz, 1H, ArH), 7.57 (m, 2H, ArH), 7.44-7.32 (m, 3H, ArH), 7.25 (m, 2H, ArH), 7.16 (d, J=8 Hz, 1H, ArH), 7.05 (dd, J=2, 8 Hz, 1H, ArH), 5.14 (s, 2H, ArCH2O), 1.65 (s, 4H, CH2CH2), 1.25 (s, 6H, 2×CH3), 1.20 (s, 6H, 2×CH3); 13C NMR (75 MHz, CDCl3) δ 190.95 (C=0), 160.72, 145.19, 144.65, 137.22, 132.97, 132.59, 131.86, 131.20, 130.00, 129.54, 128.16, 127.48, 126.71, 124.89, 123.96, 112.57, 70.50, 34.99, 34.27, 34.13, 31.83, 31.80; IR (film) 2960, 2926, 1692, 1596, 1504, 1264, 1182 cm-1 ; MS (DCI) m/e 399 (MH+), 201 (C15H21+).

Sources & evidence

ORD record: ord-a3e5c0593e70403580013f6762329878
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05391817

Reaction notes

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