Methanesulfonic Acid → HCID 59557745, 화합물

HRID 425087노트

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HRID 425087 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][O:18][CH:19]3[CH2:21][CH2:20]3)=[CH:12][CH:11]=2)[CH:3]=1.[Li][CH2:23]CCC.C[Si](C)(C)[O:29][C@@H:30]1[C@@H:35]([O:36][Si](C)(C)C)[C@H:34]([O:41][Si](C)(C)C)[C@@H:33]([CH2:46][O:47][Si](C)(C)C)[O:32][C:31]1=[O:52].CS(O)(=O)=O>C1(C)C=CC=CC=1.C1COCC1.C1(C)C=CC=CC=1.CO>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([C:31]2([O:52][CH3:23])[C@H:30]([OH:29])[C@@H:35]([OH:36])[C@H:34]([OH:41])[C@@H:33]([CH2:46][OH:47])[O:32]2)=[CH:3][C:4]=1[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][O:18][CH:19]2[CH2:21][CH2:20]2)=[CH:12][CH:11]=1

참가 물질

8

반응물 4

HCID 6395Methanesulfonic AcidHCID 10994280(3R,4S,5R,6R)-3,4,5-Tris-trimethylsilanyloxy-6-trimethylsilanyloxymethyl-tetrahydro-pyran-2-onHCID 59557748HCID 59557748, 화합물HCID 178418339Butyllithium

생성물 1

HCID 59557745HCID 59557745, 화합물

시약·촉매·용매 3

HCID 887Methanol용매HCID 1140Toluene용매HCID 22635083Tetrahydrofuran toluene용매

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온도
-65 °C

실험 절차

To a solution of 4-bromo-1-chloro-2-(4-(2-cyclopropoxyethyl)benzyl)benzene (105 mg, 0.29 mmol) in anhydrous toluene/THF (1.2 mL, v/v=2:1) was added dropwise n-BuLi (2.5 M in hexane, 0.14 mL) at −65° C., and the mixture was stirred for 30 min at −65° C. Then a −65° C. solution of (3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-((trimethylsilyloxy)methyl)tetrahydro-2H-pyran-2-one (148 mg, 0.32 mmol) in toluene (1.2 mL) was added dropwise over 15 min. The mixture was stirred at −65° C. for 3 h until starting material was consumed. The reaction was quenched with methanesulfonic acid (0.04 mL, 0.60 mmol) in methanol (1 mL), and the mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched with saturated sodium bicarbonate, the organic phase was separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with saturated bicarbonate, then with water, and then with brine, and dried over sodium sulfate. Removal of the volatiles afforded a residue (134 mg), which was used in the next step without further purification.

후처리

  1. stirringThe mixture was stirred at −65° C. for 3 h
  2. customwas consumed
  3. temperatureto warm to room temperature
  4. stirringstirred overnight
  5. customThe reaction was quenched with saturated sodium bicarbonate
  6. customthe organic phase was separated
  7. extractionthe aqueous phase was extracted with ethyl acetate
  8. washThe combined organic phases were washed with saturated bicarbonate
  9. dry with materialwith water, and then with brine, and dried over sodium sulfate
  10. customRemoval of the volatiles

출처 및 근거

ORD 기록
ord-3bc3d629ed244b0486a6d3b3c826cdc8
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106021B2

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