Triethylamine → Diethyl[3-(1-tridecynyl)phenyl]phosphonate

HRID 1647965

반응식

HRID 1647965 반응식
C([C:3]1[CH:8]=[CH:7][C:6]([P:9](=[O:12])([O-:11])[O-:10])=[C:5](CC)[C:4]=1I)C.[CH:16]#[C:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[C:29]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:30]=1.[CH2:48](N(CC)CC)[CH3:49]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:29]([O:11][P:9]([C:6]1[CH:7]=[CH:8][CH:3]=[C:4]([C:16]#[C:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:5]=1)(=[O:12])[O:10][CH2:48][CH3:49])[CH3:30]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 1177541-TridecyneHCID 86748802Diethyl-3-iodophenylphosphonate

생성물 1

HCID 9908538Diethyl[3-(1-tridecynyl)phenyl]phosphonate수율 17.7%

시약·촉매·용매 1

HCID 167845palladium(II) acetate촉매

실험 절차

Diethyl-3-iodophenylphosphonate prepared according to Example 7 (2.0 g, 5.88 mmol) and 1-tridecyne (1.79 g, 9.97 mmol) were dissolved in triethyl amine (40 ml) in a two neck round bottom flask equipped with a condenser and a nitrogen dispersing tube. The flask was inerted. Triphenylphosphine (0.047 g, 0.179 mmol) and palladium acetate (0.015 g, 0.0668 mmol) were then added and the flask was heated in an oil bath to 100° to 105° C. for 40 hours. After cooling to room temperature and filtering, the triethylamine was removed on the rotary evaporator. The residue was extracted several times with acetonitrile, and the combined extracts were stripped down to a reddish brown liquid. Chromatography on silica eluting with 20% hexane in ethyl acetate gave the product as a pale yellow oil, 0.410 g, 1.045 mmol, 17.7% yield; 1H NMR (CDCl3) ∂ 0.88 (t, J=6.8 Hz, 3H), 1.18 to 1.50 (several m, 22H), 1.60 (quint, J=7.6 Hz, 2H), 2.40 (t, J=7.1 Hz, 2H), 4.11 (m, 4H), 7.38 (m, 1H), 7.55 (br d, J=7.8 Hz, 1H), 7.71 (dd, J=13.2, 7.6 Hz, 1H), 7.83 (d, J=14.1 Hz, 1H); FAB mass spectrum m/z 399 (M+Li)+.

후처리

  1. customequipped with a condenser and a nitrogen dispersing tube
  2. temperaturethe flask was heated in an oil bath to 100° to 105° C. for 40 hours
  3. filtrationfiltering
  4. customthe triethylamine was removed on the rotary evaporator
  5. extractionThe residue was extracted several times with acetonitrile

출처 및 근거

ORD 기록
ord-3b0dd004643744b48019d6d26047b22c
출처 데이터셋
uspto-grants-1995_07
특허 번호
US05434288

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