Ethanol → HCID 18614932, compound

HRID 1265256Notes

Reaction equation

HRID 1265256 reaction equation
[CH3:1][C:2]1([CH3:29])[CH2:15][CH2:14][C:13]([CH3:17])([CH3:16])[C:12]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[C:9]3[CH:18](O)[C:19]3[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=3)=[CH:4][C:3]1=2.C([SiH](CC)CC)C.B(F)(F)F.CCOCC.CCO>ClCCl.O.CCOC(C)=O>[CH3:1][C:2]1([CH3:29])[CH2:15][CH2:14][C:13]([CH3:16])([CH3:17])[C:12]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[C:9]3[CH2:18][C:19]3[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=3)=[CH:4][C:3]1=2

Participants

8

Reactant 4

HCID 702EthanolHCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 18614954HCID 18614954, compound

Product 1

HCID 18614932HCID 18614932, compoundYield 57.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-anthracen-1-yl)-hydroxymethyl]-benzoic acid (from Example 37, 30 mg, 0.07 mmol) in dichloromethane (5 mL) was treated with excess triethylsilane (0.2 mL) and BF3-Et2O (0.16 mL) at 0° C. The solution was allowed to stir for 10 min and then EtOH was added. The mixture was diluted with water and EtOAc. The organic solution was washed with water and brine, dried (Na2SO4), filtered, and concentrated to yield 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-anthracen-1-ylmethyl)-benzoic acid (139) 15 mg (55%) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 8.01(½ABq, J=8.2 Hz, 2H, ArH), 7.81(s, 1H, ArH), 7,77(s, 1H, ArH), 7.66(d, J=8.2 Hz, 1H, ArH), 7.32(m, 3H, ArH), 7.24(s, 1H, ArH), 7.19(d, J=6.7 Hz, 1H, ArH), 4.45(s, 2H, CH2), 1.72(m, 4H, 2CH2), 1.35(s, 6H, 2CH3), 1.24(s, 6H, 2CH3).

Workup

  1. washThe organic solution was washed with water and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a18e6037c3ec495da46d74cd0475925c
Source dataset
uspto-grants-2003_04
Patent number
US06545049B1

Reaction notes

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