Water → [(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methanol

HRID 432081

反応式

HRID 432081 の反応式
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C@@H:7]([C:12](O)=[O:13])[CH2:6][CH2:5]2.B.C1COCC1.O.C([O-])(O)=O.[Na+]>C1COCC1>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C@@H:7]([CH2:12][OH:13])[CH2:6][CH2:5]2

参加物

6

反応物 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 2723981Borane;tetrahydrofuranHCID 9966213(2R)-6-Iodochromane-2-carboxylic acid

生成物 1

HCID 9943850[(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
45 °C

実験手順

To a solution of (2R)-6-iodo-3,4-dihydro-2H-chromene-2-carboxylic acid (Example 7, 19.5 mmol, 1.0 eq.) in THF (45 mL) at 10° C. was added dropwise a solution of borane-THF complex (1M in THF, 23.4 mmol, 1.2 eq). The resulting reaction mixture was stirred at 45° C. for 1.5 hours and was then cooled to 10° C. Next, water was added followed by saturated NaHCO3 solution. The resulting two-phase mixture was separated and the aqueous phase was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, concentrated to afford the product as a white solid in quantitative yield that was used without further purification. GC-MS m/z 290 (M+)

後処理

  1. customThe resulting reaction mixture
  2. temperaturewas then cooled to 10° C
  3. customThe resulting two-phase mixture was separated
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-9f9d4a6bdbcd444f8483b577369ce20a
出典データセット
uspto-grants-2003_12
特許番号
US06660752B2

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