Acetic Acid → 6-Benzyloxymethyl-2-methyl-5,6-dihydro-4H-pyran-4-one

HRID 2379169

반응식

HRID 2379169 반응식
[CH2:1]([O:8][CH2:9][CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg+2].[Br-].[Br-].C[Si](C)(C)O[CH:18]=[CH:19][C:20]([O:22][Si](C)(C)C)=[CH2:21].[CH3:29]C(O)=O>C1COCC1>[CH2:1]([O:8][CH2:9][CH:10]1[O:11][C:18]([CH3:29])=[CH:19][C:20](=[O:22])[CH2:21]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 82241Magnesium BromideHCID 108989(Phenylmethoxy)acetaldehydeHCID 544944351,3-Bis (trimethylsilyloxy)butadiene

생성물 1

HCID 199330426-Benzyloxymethyl-2-methyl-5,6-dihydro-4H-pyran-4-one수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 10.4 g of the aldehyde from Step 1 in 250 ml of THF was cooled to 0° C. and 1.0 eq. of freshly prepared MgBr2 was added dropwise. The mixture was warmed to r.t. and 40.6 g of 1,3-bis(trimethylsilyloxy)-1,3-butadiene (Emde, et al., Synthesis, p. 6 (1982)) was added. After 3 h., 50% aqueous HOAc was added and the mixture was stirred 10 min. and then extracted with Et2O (2x). After the ether was evaporated, the resultant oil was taken back up in 300 ml of CH2Cl2 and 12 ml of TFA. After 3 hours, the solution was washed with H2O, saturated NaHCO3, brine and finally dried over MgSO4. After flash chromatography, 9.5 g (60%) of the title compound was obtained.

후처리

  1. extractionextracted with Et2O (2x)
  2. customAfter the ether was evaporated
  3. waitAfter 3 hours
  4. washthe solution was washed with H2O, saturated NaHCO3, brine
  5. dry with materialfinally dried over MgSO4

출처 및 근거

ORD 기록
ord-4f201e79f89247afbe8108d2f96f8c54
출처 데이터셋
uspto-grants-1994_11
특허 번호
US05360815

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