Trimethyl borate → 2-(Cyclohexyloxy)methylphenylboronic acid

HRID 1182381노트

반응식

HRID 1182381 반응식
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[B:21](OC)([O:24]C)[O:22]C.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH:15]1([O:14][CH2:13][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[B:21]([OH:24])[OH:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

참가 물질

7

반응물 4

HCID 8470Trimethyl borateHCID 25517Ammonium ChlorideHCID 111732332-Bromobenzyl cyclohexyl etherHCID 178418339Butyllithium

생성물 1

HCID 112877352-(Cyclohexyloxy)methylphenylboronic acid

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

31.2 ml of n-butyllithium (1.6 M) in solution in n-hexane are added dropwise at −70° C. to 13.45 g of 1-bromo-2-[(cyclohexyloxy)methyl]benzene, obtained in step 1.1, in solution in 150 ml of tetrahydrofuran. After 2 hours at −70° C., 10.2 ml of trimethyl borate are introduced dropwise and the temperature of the reaction medium is allowed to rise to −30° C. The medium is hydrolyzed with a saturated ammonium chloride solution, and then extracted with ethyl acetate and the organic phase is dried with anhydrous sodium sulfate. After evaporation, 11.7 g of a yellow oil are obtained.

후처리

  1. customto rise to −30° C
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic phase is dried with anhydrous sodium sulfate
  4. customAfter evaporation, 11.7 g of a yellow oil
  5. customare obtained

출처 및 근거

ORD 기록
ord-cd41308fdbf04148a272fb1fa07e9833
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288659B2

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