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Potassium Carbonate → Methyl 3-benzyloxy-5-phenylbenzoate

HRID 1431001
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인쇄 미리보기

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HRID 1431001 반응식
C1COCC1.O.[CH3:7][O:8][C:9](=[O:32])[C:10]1[CH:15]=[C:14](OS(C(F)(F)F)(=O)=O)[CH:13]=[C:12]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:11]=1.[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:7][O:8][C:9]([C:10]1[CH:15]=[C:14]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:13]=[C:12]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:11]=1)=[O:32]
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참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 18945283Methyl 3-benzyloxy-5-(trifluoromethanesulfonyloxy)benzoateHCID 21881883Oxolane--water (1/1)

생성물 1

HCID 18945315Methyl 3-benzyloxy-5-phenylbenzoate수율 90.8%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 3283Diethyl Ether용매

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온도
130 °C

실험 절차

To a mixture of THF/H2O (5 mL, v/v=4:1) in a microwave vial was added 3-benzyloxy-5-trifluoromethanesulfonyloxy-benzoic acid methyl ester (100 mg, 0.256 mmol), phenylboronic acid (34 mg, 0.281 mmol), potassium carbonate (71 mg, 0.512 mmol), and Pd(PPh3)4 (15 mg, 0.02 mmol). The reaction vessel was sealed and subjected to microwave heating for 5 min at 130° C. After cooling, it was diluted with diethyl ether and washed with brine, dried (MgSO4), and evaporated. The residue was subjected to chromatography on silica gel using an ethyl acetate-hexane gradient to afford 74 mg (90%) of 5-benzyloxybiphenyl-3-carboxylic acid methyl ester: LCMS m/z=319.4 [C21H18O3+H]+.

후처리

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

출처 및 근거

ORD 기록
ord-792c66f82eed4a06b8ff532e1d0997ab
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08940927B2

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