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

HRID 20500

반응식

HRID 20500 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-f9de1b9e97054b5aaabc4d4e3ea7f6bd
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745475B2

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