Hydrochloric Acid → (+/-)-3-(2,4-Dihydroxyphenyl)-1-methylcyclohexanol

HRID 585699노트

반응식

HRID 585699 반응식
[CH3:1][Mg]Cl.[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[CH:12]1[CH2:17][CH2:16][CH2:15][C:14](=[O:18])[CH2:13]1.Cl>O1CCCC1>[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[CH:12]1[CH2:17][CH2:16][CH2:15][C:14]([CH3:1])([OH:18])[CH2:13]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 12788196(+/-)-3-(2,4-Dihydroxyphenyl)cyclohexanoneHCID 178418332HCID 178418332, 화합물

생성물 1

HCID 22337786(+/-)-3-(2,4-Dihydroxyphenyl)-1-methylcyclohexanol수율 28%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Methyl magnesium chloride (0.132 ml of a 22% w/w solution in tetrahydrofuran) was added to a solution of (±)-3-(2,4-dihydroxyphenyl)cyclohexanone (20 mg) in tetrahydrofuran (3 ml) at 0° C. under argon. After 16 hr, dilute hydrochloric acid (1 ml) was added dropwise and the reaction mixture was partitioned between ethyl acetate (50 ml) and brine (50 ml). The aqueous layer was extracted with ethyl acetate (2×50 ml), and the combined organic extracts were dried over magnesium sulfate and evaporated in vacuo. The crude residue was purified by preparative HPLC to furnish the title compound as a white solid (6 mg, 28%). δH (d4-MeOH) 1.20 (3H, s), 1.22-1.39 (2H, overlapping m), 1.46 (1H, t), 1.54-1.87 (5H, overlapping m), 3.22 (1H, m), 6.19-6.25 (2H, overlapping m), 6.86 91H, d); m/z (ES−) 281 (M+60−H)−.

후처리

  1. customthe reaction mixture was partitioned between ethyl acetate (50 ml) and brine (50 ml)
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×50 ml)
  3. dry with materialthe combined organic extracts were dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe crude residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-9edc428806434618b2dab1a0861467a1
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06933319B2

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