Triphenylphosphine → Methyl 3-(benzyloxy)-5-[(1S)-2-methoxy-1-methylethoxy]benzoate

HRID 20500ノート

反応式

HRID 20500 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:39][O:40][CH2:41][C@H:42](O)[CH3:43].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:39][O:40][CH2:41][C@@H:42]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH3:43]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 2733589(R)-(-)-1-Methoxy-2-propanolHCID 5363146Diisopropyl azodicarboxylateHCID 7472028Methyl 3-(benzyloxy)-5-hydroxybenzoate

生成物 1

HCID 59127167Methyl 3-(benzyloxy)-5-[(1S)-2-methoxy-1-methylethoxy]benzoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl 3-hydroxy-5-{[phenylmethyl]oxy}benzoate (77.4 mmol) in THF was added polymer-supported triphenylphosphine (51.7 g of 3 mmol/g loading, 155 mmol) and (R)-(−)-1-methoxy-2-propanol (102 mmol). The stirred solution was blanketed with argon and cooled in an ice bath. A solution of DIAD (116 mmol) was added dropwise by syringe over 10 minutes. The solution was stirred for 20 minutes and filtered, washing the residue with THF (500 mL). The filtrate and washings were combined, and evaporated to give the desired compound which was used without further purification.

後処理

  1. temperaturecooled in an ice bath
  2. filtrationfiltered
  3. washwashing the residue with THF (500 mL)
  4. customevaporated

出典と根拠

ORDレコード
ord-f9de1b9e97054b5aaabc4d4e3ea7f6bd
出典データセット
uspto-grants-2010_06
特許番号
US07745475B2

反応ノート

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