Boron trifluoride etherate → HCID 9828518, compound

HRID 1008304Notes

Reaction equation

HRID 1008304 reaction equation
C[O:2][C:3](=[O:46])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([O:28]CC3C=CC=CC=3)[C:25]([C:36]3[N:37]=[CH:38][S:39][CH:40]=3)=[CH:24][C:23]=2[CH2:41][CH3:42])[C:12]=1[CH2:43][CH2:44][CH3:45].B(F)(F)F.CCOCC>C(S)C.C(OCC)C>[CH2:41]([C:23]1[CH:24]=[C:25]([C:36]2[N:37]=[CH:38][S:39][CH:40]=2)[C:26]([OH:28])=[CH:27][C:22]=1[O:21][CH2:20][CH2:19][CH2:18][O:17][C:13]1[C:12]([CH2:43][CH2:44][CH3:45])=[C:11]([CH:16]=[CH:15][CH:14]=1)[O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([OH:46])=[O:2])[CH3:42]

Participants

5

Reactant 2

HCID 8000Boron trifluoride etherateHCID 601111882-{3-[3-(5-Benzyloxy-2-ethyl-4-thiazol-4-yl-phenoxy)propoxy]-2-propyl-phenoxy}benzoic acid methyl ester

Product 1

HCID 9828518HCID 9828518, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6343EthanethiolSolvent

Procedure

A solution of 2-{3-[3-(5-benzyloxy-2-ethyl-4-thiazol-4-yl-phenoxy)propoxy]-2-propyl-phenoxy}benzoic acid methyl ester (243 mg, 0.366 mmol) in ethanethiol (7 mL) was treated with boron trifluoride etherate at room temperature for 4 h. The mixture was diluted with diethyl ether, washed once with water, once with saturated sodium bicarbonate solution, dried (sodium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, 15% ethyl acetate/85% hexane) of the residue provided 131 mg (65%) of the title compound as a colorless oil. 1H NMR (CDCl3) δ 8.88 (d, J=1 Hz, 1H), 7.88 (dd, J=8, 1 Hz, 1H), 7.44 (d, J=1 Hz, 1H), 7.38 (m, 2H), 7.08 (m, 2H), 6.81 (d, J=8 Hz, 1H), 6.68 (d. J=8 Hz, 1H), 6.55 (s, 1H), 6.43 (d, J=8 Hz, 1H), 4.21 (t, J=6 Hz, 4H), 3.83 (s, 3H), 2.63 (m, 4H), 2.33 (quintet, J=6 Hz, 2H), 1.56 (hextet, J=8 Hz, 2H), 1.19 (t, J=8 Hz, 3H), 0.91 (t, J=7 Hz, 3H); TOF MS ES+ exact mass calculated for C31H34NO6S (p+1): m/z=548.2107. Found: 548.2085.

Workup

  1. washwashed once with water, once with saturated sodium bicarbonate solution
  2. dry with materialdried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cfaf39b120f443aab89a80285acc1522
Source dataset
uspto-grants-2004_09
Patent number
US06797723B1

Reaction notes

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