Sodium borohydride → HCID 86694794, 화합물

HRID 2273380노트

반응식

HRID 2273380 반응식
[CH3:1][CH:2]1[C:19](=O)[C:5]2=[CH:6][C:7]3[C:8]([CH3:18])([CH3:17])[C:9]4[C:14]([C:15]=3[CH:16]=[C:4]2[CH2:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=4.[BH4-].[Na+]>C1COCC1.C(O)C.C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][C:2]1[CH2:3][C:4]2[C:5]([CH:19]=1)=[CH:6][C:7]1[C:8]([CH3:18])([CH3:17])[C:9]3[C:14]([C:15]=1[CH:16]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3

참가 물질

7

반응물 2

HCID 4311764Sodium borohydrideHCID 71089313HCID 71089313, 화합물

생성물 1

HCID 86694794HCID 86694794, 화합물수율 89.5%

시약·촉매·용매 4

HCID 6101p-Toluenesulfonic acid촉매HCID 702Ethanol용매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

In a 1000 mL round flask, 2,9,9-trimethyl-2,3-dihydrocyclopenta[b]fluoren-1(9H)-one (50 g, 190.6 mmol) was dissolved THF 400 mL and ethanol 400 mL, and then stirred. Sodium borohydride (NaBH4) (9.4 g, 247.8 mmol) was added to the reaction product in five lots, and then stirred for 12 hours. The resultant mixture, after removal of solvent, was dissolved in ethylacetate, and then washed with water three times. The organic layer was dried over magnesium sulfate, followed by removal of volatile materials. The dried reaction product was dissolved in 320 mL of toluene, and then inputted to a 500 mL round flask. After that, p-toluene sulfonic acid (0.2 g) was inputted thereto, and then water was completely removed under reflux with Dean-Stark. The resultant material was cooled to room temperature, and then an aqueous ammonium chloride solution (150 mL) and 200 mL of diethyl ether were injected thereto, followed by separation of the organic layer. The organic layer collected by extracting the residue with diethyl ether was dried over magnesium sulfate, followed by removal of volatile materials, and then purified by using silica gel column chromatography, to thereby obtain 42.0 g of 2,9,9-trimethyl-3,9-dihydrocyclopenta[b]fluorene (yield: 89.42%).

후처리

  1. stirringstirred for 12 hours
  2. customThe resultant mixture, after removal of solvent
  3. dissolutionwas dissolved in ethylacetate
  4. washwashed with water three times
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customfollowed by removal of volatile materials
  7. customThe dried reaction product
  8. custominputted to a 500 mL round flask
  9. customwater was completely removed
  10. temperatureunder reflux with Dean-Stark
  11. customfollowed by separation of the organic layer
  12. customThe organic layer collected
  13. extractionby extracting the residue with diethyl ether
  14. dry with materialwas dried over magnesium sulfate
  15. customfollowed by removal of volatile materials
  16. custompurified

출처 및 근거

ORD 기록
ord-eecc7747ea7f494dbd0901b46442d5b1
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120884B2

반응 노트

불러오는 중…