Sodium Hydroxide → (-)-5-Decyloxy-2-[4-(6-hydroxyheptenyl)phenyl]pyrimidine

HRID 1956084노트

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HRID 1956084 반응식
[CH2:1]([O:11][C:12]1[CH:13]=[N:14][C:15]([C:18]2[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=2)=[N:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH-].[Na+].[OH:27][CH:28]([CH3:34])[CH2:29][CH2:30][CH2:31][C:32]#[CH:33].[B]1OC2C(=CC=CC=2)O1>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C1(C)C=CC=CC=1>[CH2:1]([O:11][C:12]1[CH:13]=[N:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([CH:33]=[CH:32][CH2:31][CH2:30][CH2:29][CH:28]([OH:27])[CH3:34])=[CH:20][CH:19]=2)=[N:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

참가 물질

9

반응물 4

HCID 14798Sodium HydroxideHCID 6327445BenzcatechinboraneHCID 114747935-Decyloxy-2-(4-bromophenyl)pyrimidineHCID 133371736-Heptyn-2-ol

생성물 1

HCID 53726462(-)-5-Decyloxy-2-[4-(6-hydroxyheptenyl)phenyl]pyrimidine

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매2회

실험 절차

In a reactor equipped with a stirrer and a thermometer, 5-decyloxy-2-(4-bromophenyl)pyrimidine (13.98 g), dry tetrahydrofuran (THF) (30 ml), tetrakis(triphenylphosphine)palladium (0.11 g) and sodium hydroxide (1.2 g) are charged. To the mixture, a solution of a reaction product of 6-hydroxy-1-heptyne and catechol borane (5 g) dissolved in THF (12 ml) is dropwise added, followed by heating up to a refluxing temperatur. After reacting for 4 hours, the reaction mixture is cooled to room temperature. To the mixture, toluene and water are added for extraction, and the organic layer is washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. A resulting residue is purified by silica gel column chromatography (eluent: toluene-ethyl acetate) to obtain (-)-5-decyloxy-2-[4-(6-hydroxyheptenyl)phenyl]pyrimidine (7.99 g).

후처리

  1. customIn a reactor equipped with a stirrer
  2. additionis dropwise added
  3. temperatureby heating up to a refluxing temperatur
  4. washthe organic layer is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customA resulting residue is purified by silica gel column chromatography (eluent: toluene-ethyl acetate)

출처 및 근거

ORD 기록
ord-8a8ce80cea944b04bf606a5037419e41
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05779934

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