Dichloromethane → 1,2,3,4-Tetrahydro-8-methyl-1-naphthalenemethanol

HRID 729774ノート

反応式

HRID 729774 の反応式
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]([C:12](O)=[O:13])[CH2:9][CH2:8][CH2:7]2.ClCCl>O1CCCC1>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]([CH2:12][OH:13])[CH2:9][CH2:8][CH2:7]2

参加物

4

反応物 2

HCID 6344DichloromethaneHCID 12778763HCID 12778763、化合物

生成物 1

HCID 118052711,2,3,4-Tetrahydro-8-methyl-1-naphthalenemethanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

8-Methyl-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid (J. Org. Chem. 1982, 47, 2590-2593) (0.066 g, 0.34 mmol) was dissolved in tetrahydrofuran (3 mL). To the solution was then added at 0° C. a 1.0M solution of borane-methyl sulfide complex in dichloromethane (0.7 mL, 0.69 mmol). The reaction mixture was stirred at room temperature for 15 minutes, refluxed for 2 hrs, then cooled down to 0° C. and quenched with methanol. The solvent was then evaporated in vacuo to yield a crude oil. The crude oil was partitioned with water and diethyl ether. The organic layer was dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield crude (8-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-methanol as an oil which was used directly to the next step.

後処理

  1. temperaturerefluxed for 2 hrs
  2. temperaturecooled down to 0° C.
  3. customquenched with methanol
  4. customThe solvent was then evaporated in vacuo
  5. customto yield a crude oil
  6. customThe crude oil was partitioned with water and diethyl ether
  7. dry with materialThe organic layer was dried with Na2SO4
  8. filtrationfiltered
  9. customthe solvent evaporated in vacuo

出典と根拠

ORDレコード
ord-0899306fd8b74cb4a68aec38acf29d53
出典データセット
uspto-grants-2009_09
特許番号
US07582649B2

反応ノート

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