Triethylamine → Racemic Binaphthol Dinonaflate

HRID 50151

반응식

HRID 50151 반응식
[F:1][C:2]([F:17])([C:13]([F:16])([F:15])[F:14])[C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[S:5](F)(=[O:7])=[O:6].[C:18]1([C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:32]=[CH:31][CH:30]=2)[C:19]([OH:28])=[CH:20][CH:21]=[C:22]2[C:27]=1[CH:26]=[CH:25][CH:24]=[CH:23]2.C(N(CC)CC)C.[OH-:46].[Na+]>ClCCl.O>[S:5]([C:4]([C:3]([C:2]([C:13]([F:16])([F:15])[F:14])([F:17])[F:1])([F:12])[F:11])([F:10])[F:9])([OH:28])(=[O:7])=[O:6].[S:5]([C:4]([C:3]([C:2]([C:13]([F:14])([F:15])[F:16])([F:1])[F:17])([F:12])[F:11])([F:10])[F:9])([OH:7])(=[O:6])=[O:46].[C:18]1([C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:32]=[CH:31][CH:30]=2)[C:19]([OH:28])=[CH:20][CH:21]=[C:22]2[C:27]=1[CH:26]=[CH:25][CH:24]=[CH:23]2

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 27552601-(1-Naphthyl)-2-naphthol

생성물 1

HCID 131724384Racemic Binaphthol Dinonaflate

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

111.6 g of nonafluoro-n-butanesulfonyl fluoride (370 mmol) were added at room temperature to a solution of 45.6 g of racemic binaphthol (160 mmol) and 47.6 g of triethylamine (470 mmol; 65.5 ml) in 350 ml of dichloromethane. After a few minutes, the denser sulfonyl phase had disappeared, without the mixture warming appreciably. After stirring for 4 hours, the mixture was shaken once with 80 ml of aqueous sodium hydroxide solution (5% by weight) and once with 80 ml of water, and the organic phase was dried over sodium sulfate and concentrated on a rotary evaporator. The product crystallized out on cooling and was purified further by washing with a small amount of cold methanol and subsequent filtration with suction. This gave 123 g of binaphthol dinonaflate (90.0%) as colourless crystals having a melting point of 104.1° C.; HPLC purity>99% (RP-18; methanol/water 80:20; 254 nm)

후처리

  1. waitAfter a few minutes
  2. temperaturewarming appreciably
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. concentrationconcentrated on a rotary evaporator
  5. customThe product crystallized out
  6. temperatureon cooling
  7. customwas purified further
  8. washby washing with a small amount of cold methanol and subsequent filtration with suction

출처 및 근거

ORD 기록
ord-c9e773387fca48069b8381f0d8e7174a
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710198B2

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