Pyridine 4-methylbenzene-1-sulfonate → 7-Phenylhept-6-yn-1-ol

HRID 269425

반응식

HRID 269425 반응식
C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1.[C:18]1([C:24]#[C:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31]C2CCCCO2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CO>[C:18]1([C:24]#[C:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][OH:31])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

4

반응물 2

HCID 161440Pyridine 4-methylbenzene-1-sulfonateHCID 589246782-(7-phenylhept-6-ynyloxy)tetrahydro-2H-pyrane

생성물 1

HCID 589246797-Phenylhept-6-yn-1-ol수율 97%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
55 °C

실험 절차

Pyridine toluene-4-sulphonate (0.75 g, 3 mmol) was added to a magnetically stirred solution of 2-(7-phenylhept-6-ynyloxy)-tetrahydro-2H-pyrane (7) (13.62 g, 50 mmol) in dry methanol (300 mL). The reaction mixture was stirred at 55° C. and monitored by TLC. When all the base material had been converted, methanol was distilled out on a rotary evaporator and water (200 mL) was added to the residue. The aqueous phase was extracted with petroleum ether (boiling point 40-60° C.)/Et2O 1:1 (5×50 mL). The combined organic phases were washed with water (2×20 mL) and dried (MgSO4). Distillation on a rotary evaporator yielded 9.1 g (97%) of a yellow viscous oil. TLC and NMR indicated a pure product.

후처리

  1. distillationmethanol was distilled out on a rotary evaporator and water (200 mL)
  2. additionwas added to the residue
  3. extractionThe aqueous phase was extracted with petroleum ether (boiling point 40-60° C.)/Et2O 1:1 (5×50 mL)
  4. washThe combined organic phases were washed with water (2×20 mL)
  5. dry with materialdried (MgSO4)
  6. distillationDistillation
  7. customon a rotary evaporator

출처 및 근거

ORD 기록
ord-2facfffb0e2d44a9892ae3ed367c9f35
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446226B2

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