Water → 4-{4-Hydroxy-1-[4-(tetrahydro-2h-pyran-2-yloxy)phenoxy]butyl}-benzonitrile

HRID 411538ノート

反応式

HRID 411538 の反応式
B.CSC.[O:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[O:11][C:12]1[CH:30]=[CH:29][C:15]([O:16][CH:17]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)[CH2:18][CH:19]=[CH2:20])=[CH:14][CH:13]=1.O.CC[O:34]CC>C1COCC1>[OH:34][CH2:20][CH2:19][CH2:18][CH:17]([C:21]1[CH:22]=[CH:23][C:24]([C:25]#[N:26])=[CH:27][CH:28]=1)[O:16][C:15]1[CH:29]=[CH:30][C:12]([O:11][CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][O:5]2)=[CH:13][CH:14]=1

参加物

6

反応物 4

HCID 962WaterHCID 3283Diethyl EtherHCID 12423031(Dimethyl sulfide)trihydroboronHCID 222356714-{1-[4-(Tetrahydro-2H-pyran-2-yloxy)phenoxy]-3-butenyl}benzonitrile

生成物 1

HCID 222354084-{4-Hydroxy-1-[4-(tetrahydro-2h-pyran-2-yloxy)phenoxy]butyl}-benzonitrile収率 58%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Borane-dimethylsulfide complex (3.5 mL of 2 M in ether, 7 mmol) was added dropwise to a cooled (5° C.) solution of 4-{1-[4-(tetrahydro-2H-pyran-2-yloxy)phenoxy]-3-butenyl}benzonitrile (see step (i) above; 4.6 g, 13 mmol) in dry THF over a period of 15 min. The resulting mixture was stirred at between 0 and 5° C. for 1.5 h. Stirring was then continued for a further 4 h at rt. Water (14 mL) and NaBO3 (5 g) were added and the mixture stirred overnight. Ether was added and the resulting organic layer was separated, washed with water and brine, dried and then evaporated. The resulting residue was purified by chromatography on silica gel, eluting with IPA:EtOAc:heptane (5:20:70), to give 2.44 g (58%) of the sub-title compound.

後処理

  1. stirringStirring
  2. waitwas then continued for a further 4 h at rt
  3. stirringthe mixture stirred overnight
  4. customthe resulting organic layer was separated
  5. washwashed with water and brine
  6. customdried
  7. customevaporated
  8. customThe resulting residue was purified by chromatography on silica gel
  9. washeluting with IPA:EtOAc:heptane (5:20:70)

出典と根拠

ORDレコード
ord-a7c7ce7d0bff421ebc4c7b1491249170
出典データセット
uspto-grants-2003_05
特許番号
US06559162B2

反応ノート

読み込み中…