(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexane-1-carbaldehyde → 1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)but-3-yn-1-ol

HRID 546373노트

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HRID 546373 반응식
[CH:1]([C@@H:4]1[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6][C@H:5]1[CH:11]=[O:12])([CH3:3])[CH3:2].[CH2:13]([Mg]Br)[C:14]#[CH:15]>C1COCC1>[CH:1]([C@@H:4]1[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6][C@H:5]1[CH:11]([OH:12])[CH2:15][C:14]#[CH:13])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 11252239(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexane-1-carbaldehydeHCID 178455849HCID 178455849, 화합물2회

생성물 1

HCID 866439371-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)but-3-yn-1-ol수율 37.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of (1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarbaldehyde (1.0 g, 6.0 mmol) in THF (10 mL) at 0° C. was slowly added propargyl magnesium bromide (1 M, 8.9 mmol). After the reaction was allowed to warm to room temperature overnight 1.5 equivalents of additional propargyl magnesium bromide were added and the reaction was allowed to stir for 6 additional h. The reaction was again cooled to 0° C. and then quenched with 1 N HCl and partitioned between brine and MTBE. The organic layer was dried (MgSO4) and concentrated. The residue was purified by silica chromatography to give the desired alcohol (0.47 g).

후처리

  1. customat 0° C.
  2. additionwere added
  3. customquenched with 1 N HCl
  4. custompartitioned between brine and MTBE
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica chromatography

출처 및 근거

ORD 기록
ord-345f706e4ffc4137be4f291a604843b2
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935848B2

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