Sodium Chloride → 3,4,5-Triacetoxy-6-(2-formyl-thiophen-3-yloxy)-tetrahydropyran-2-ylmethyl acetate

HRID 1445328

Reaction equation

HRID 1445328 reaction equation
OC1C=CSC=1C=O.[C:9]([O:12][CH:13]1[CH:18]([O:19][C:20](=[O:22])[CH3:21])[CH:17]([O:23][C:24](=[O:26])[CH3:25])[CH:16]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[O:15][CH:14]1[O:32][C:33]1[CH:37]=[C:36](C(C)C)[S:35][C:34]=1[C:41](=[O:50])C1C=CC(OC)=CC=1)(=[O:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.ClCCl.O>[C:9]([O:12][CH:13]1[CH:18]([O:19][C:20](=[O:22])[CH3:21])[CH:17]([O:23][C:24](=[O:26])[CH3:25])[CH:16]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[O:15][CH:14]1[O:32][C:33]1[CH:37]=[CH:36][S:35][C:34]=1[CH:41]=[O:50])(=[O:11])[CH3:10]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 21045301(4,5-Diacetoxy-6-acetoxymethyl-2-[5-isopropyl-2-(4-methoxy-benzoyl)-thiophen-3-yloxy]-tetrahydro-pyran-3-yl) acetateHCID 1357421533-Hydroxythiophene-2-carbaldehyde

Product 1

HCID 219612443,4,5-Triacetoxy-6-(2-formyl-thiophen-3-yloxy)-tetrahydropyran-2-ylmethyl acetate

Reagents, catalysts & solvents 3

HCID 159952Benzyltributylammonium chlorideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

3.81 g of 3-hydroxy-thiophene-2-carbaldehyde, 30.5 g of (4,5-diacetoxy-6-acetoxymethyl-2-[5-isopropyl-2-(4-methoxy-benzoyl)-thiophen-3-yloxy]-tetrahydro-pyran-3-yl) actate, 37.0 g of potassium carbonate and 9.2 g of benzyltributylammonium chloride were dissolved in 850 ml of dichloromethane. 7.5 ml of water were added, and the reaction mixture was stirred for 60 h. The solution was extraced with water and saturated sodium chloride solution, and the organic phase was dried over sodium sulfate and evaporated. 60 ml of ethanol:water (9:1) were added to the resulting brownish foam, and the resulting fine precipitate was filtered off with suction. The product with the molecular weight: 458.44 (C19H22O11S), MS (ESI): 476 (M+NH4+) was obtained.

Workup

  1. dry with materialthe organic phase was dried over sodium sulfate
  2. customevaporated
  3. addition60 ml of ethanol:water (9:1) were added to the resulting brownish foam
  4. filtrationthe resulting fine precipitate was filtered off with suction
  5. customThe product with the molecular weight: 458.44 (C19H22O11S), MS (ESI): 476 (M+NH4+) was obtained

Sources & evidence

ORD record
ord-eb3df8f559ea4774ae756a40bd98ec34
Source dataset
uspto-grants-2010_02
Patent number
US07666848B2

Linked notes

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