Trimethyl phosphonoacetate → HCID 53792784, compound

HRID 964497Notes

Reaction equation

HRID 964497 reaction equation
[CH3:1][O:2][C:3]([CH2:5]P(OC)(OC)=O)=[O:4].[Li]CCCC.[CH3:17][C:18]1([CH3:35])[CH2:31][CH2:30][C:29]([CH3:33])([CH3:32])[C:28]2[CH:27]=[C:26]3[C:21]([CH2:22][CH2:23][CH2:24][C:25]3=O)=[CH:20][C:19]1=2>C1COCC1>[CH3:32][C:29]1([CH3:33])[CH2:30][CH2:31][C:18]([CH3:35])([CH3:17])[C:19]2[CH:20]=[C:21]3[C:26]([CH2:25][CH2:24][CH:23]=[C:22]3[CH2:5][C:3]([O:2][CH3:1])=[O:4])=[CH:27][C:28]1=2

Participants

5

Reactant 3

HCID 80029Trimethyl phosphonoacetateHCID 30229693,4,5,6,7,8-Hexahydro-5,5,8,8-tetramethylanthracen-1(2H)-oneHCID 178418339Butyllithium

Product 1

HCID 53792784HCID 53792784, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of trimethyl phosphonoacetate (5.68 g, 31 mmol) in THF (15 ml) was added dropwise nBuLi (9.3 ml, 2.5 M, 23 mM) at 0° C., and the resulting solution was stirred at that temperature for 30 min. 3,4,5,6,7,8-hexahydro-5,5,8,8-tetramethyl-2H-anthracen-1-one (2.0 g, 7.8 mmol) in THF (10 ml) was added at 25° C., and the mixture was stirred at that temperature for 30 min. Standard work-up procedures as detailed in Example 1, followed by purification of the product by column chromatography (10% ether in hexane) gave methyl (3,4,5,6,7,8-hexahydro-5,5,8,8-tetramethylanthracen-1-yl)acetate (1.33 g, 55%): 1H NMR (400 MHz, CDCl3) δ 7.15 (s, 1H, ArH), 7.04 (s, 1H, ArH), 5.94 (br t, 1H, olefinic), 3.68 (s, 2H, OCH3), 3.43 (s, 2H, CH2), 2.74 (t, J=7.9 Hz, 2H, CH2, benzylic), 2.31 (m, CH2, 2H, allylic), 1.66 (s, 4H, 2CH2), 1.27 (s, 12H, 4CH3).

Workup

  1. stirringthe mixture was stirred at that temperature for 30 min
  2. customfollowed by purification of the product by column chromatography (10% ether in hexane)

Sources & evidence

ORD record
ord-0e1385693e844f4ba7a32e578bf2f545
Source dataset
uspto-grants-1998_06
Patent number
US05770378

Reaction notes

Loading…