Hydrochloric Acid → t-butyl 3-hydroxy-(R)-5-[(tetrahydro-2H-pyran-2-yl) oxy]-2-[(S)-p-tolylsulfinyl]-hexadecanoate

HRID 6054ノート

反応式

HRID 6054 の反応式
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([S@:7]([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:8])=[CH:3][CH:2]=1.C([Mg]Br)(C)(C)C.[O:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]1[O:30][C@H:31]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:32][CH:33]=[O:34].Cl>CCOCC.C1COCC1>[OH:34][CH:33]([CH2:32][CH:31]([O:30][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][O:24]1)[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[C@@H:9]([S@@:7]([C:4]1[CH:3]=[CH:2][C:1]([CH3:17])=[CH:6][CH:5]=1)=[O:8])[C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 11118618t-butyl [(S)-p-tolylsulfinyl]acetateHCID 14852578(R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]tetradecanalHCID 178418586HCID 178418586、化合物

生成物 1

HCID 67855726t-butyl 3-hydroxy-(R)-5-[(tetrahydro-2H-pyran-2-yl) oxy]-2-[(S)-p-tolylsulfinyl]-hexadecanoate収率 67%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

G)a) 16.5 g of t-butyl [(S)-p-tolylsulfinyl]acetate were dissolved in a mixture of 600 ml of ether and 60 ml of THF and cooled to -78° C. 43 ml of t-butylmagnesium bromide were then added dropwise in such a manner that the temperature remained below -70° C. After stirring at -78° C. for 1 hour 13.4 g of (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-tetradecanal in 100 ml of THF were added dropwise. After 2 hours at -78° C. the reaction mixture was hydrolyzed with 2N hydrochloric acid and the solvent was evaporated off. The reaction mixture remaining behind was extracted with ether and the ethereal phase was dried and evaporated. After chromatography on silica gel there were obtained 14.9 g of t-butyl 3-hydroxy-(R)-5-[(tetrahydro-2H-pyran-2-yl)oxy]-2-[(S)-p-tolylsulfinyl]-hexadecanoate (67% yield). m.p. 97°-98° C.

後処理

  1. customremained below -70° C
  2. additionwere added dropwise
  3. customthe solvent was evaporated off
  4. extractionThe reaction mixture remaining behind was extracted with ether
  5. customthe ethereal phase was dried
  6. customevaporated

出典と根拠

ORDレコード
ord-c04649af83bc427ba93579ecd97a2120
出典データセット
uspto-grants-1993_09
特許番号
US05246960

反応ノート

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