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

HRID 2379169

反応式

HRID 2379169 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4f201e79f89247afbe8108d2f96f8c54
出典データセット
uspto-grants-1994_11
特許番号
US05360815

関連ノート

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