Methanol → HCID 29921578、化合物

HRID 1255179ノート

反応式

HRID 1255179 の反応式
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:21]=[CH:20][C:14]([C:15](OCC)=[O:16])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.CC(C[AlH]CC(C)C)C.CO>C1COCC1.CCOCC.[Na].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[K+]>[O:1]1[C:5]2([CH2:6][CH2:7][CH:8]([C:11]3[CH:12]=[CH:13][C:14]([CH2:15][OH:16])=[CH:20][CH:21]=3)[CH2:9][CH2:10]2)[O:4][CH2:3][CH2:2]1

参加物

7

反応物 3

HCID 887MethanolHCID 14487Diisobutylaluminum hydrideHCID 29921579Ethyl 4-(1,4-dioxaspiro[4.5]dec-8-yl)benzoate

生成物 1

HCID 29921578HCID 29921578、化合物

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 86594854HCID 86594854、化合物溶媒

実験手順

To a cooled (−78° C.) solution of the title compound from Example 10 Step B (450 mg, 1.55 mmol) in THF (8 mL) was added DIBAL-H (3.10 mL, 1.50 M in heptane, 4.65 mmol). After 30 min, the reaction mixture was transferred to a 0° C. bath and was held at this temperature for 45 min, whereupon it was quenched by addition of MeOH (0.63 mL, 15.5 mmol). The resulting mixture was diluted with ether and saturated aqueous sodium/potassium tartrate, and the mixture was stirred rapidly until a clear phase separation was achieved. The organic phase was separated, dried over anhydrous sodium sulfate, and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 30% EtOAc in hexanes, then 30 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 231.1 [M−OH]+; 1H NMR (500 MHz, CDCl3) δ 7.29 (d, J=7.5 Hz, 2H), 7.24 (d, J=7.5 Hz, 2H), 4.65 (s, 2H), 3.98 (s, 4H), 2.59-2.54 (m, 1H), 1.87-1.66 (m, 8H).

後処理

  1. customwas transferred to a 0° C.
  2. waitwas held at this temperature for 45 min, whereupon it
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel (0 to 30% EtOAc in hexanes

出典と根拠

ORDレコード
ord-5e11821fa3c8413cba35e959a60be11e
出典データセット
uspto-grants-2013_06
特許番号
US08455638B2

反応ノート

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