Pyridine → (1R,2S,4R)-2-Acetoxy-4-methyl-cyclohexanecarboxylic acid

HRID 1808001노트

반응식

HRID 1808001 반응식
[OH:1][C@H:2]1[CH2:7][C@H:6]([CH3:8])[CH2:5][CH2:4][C@H:3]1[C:9]([OH:11])=[O:10].N1C=CC=CC=1.[C:18](OC(=O)C)(=[O:20])[CH3:19]>ClCCl>[C:18]([O:1][C@H:2]1[CH2:7][C@H:6]([CH3:8])[CH2:5][CH2:4][C@H:3]1[C:9]([OH:11])=[O:10])(=[O:20])[CH3:19]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 45084907(1r,2s,4r)-2-Hydroxy-4-methylcyclohexanecarboxylic acid

생성물 1

HCID 57457642(1R,2S,4R)-2-Acetoxy-4-methyl-cyclohexanecarboxylic acid수율 53.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (1R,2S,4R)-2-Hydroxy-4-methyl-cyclohexanecarboxylic acid (162 mg, 1.02 mmol) in dichloromethane (5 ml) was added pyridine (495 ul, 6.12 mmol) followed by acetic anhydride (385 ul, 4.08 mmol). The reaction mixture was stirred for 20 h at room temperature. Then, the solvents were removed and 10 ml of 3N HCl solution was added. This mixture was stirred for 30 minutes and then a saturated solution of NaHCO3 was slowly added until PH=9-10. This solution was then extracted with ethyl acetate (2×5 ml). The aqueous phase was then acidified with a 10% HCl solution and extracted with ethyl acetate (3×5 ml). The following ethyl acetate layers were combined, dried (Na2SO4) and concentrated to obtain 109 mg (53%) of (1R,2S,4R)-2-Acetoxy-4-methyl-cyclohexanecarboxylic acid.

후처리

  1. customThen, the solvents were removed
  2. addition10 ml of 3N HCl solution was added
  3. stirringThis mixture was stirred for 30 minutes
  4. additiona saturated solution of NaHCO3 was slowly added until PH=9-10
  5. extractionThis solution was then extracted with ethyl acetate (2×5 ml)
  6. extractionextracted with ethyl acetate (3×5 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-44200983232549efbc5363f2df04bb12
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08357718B2

반응 노트

불러오는 중…