Diethyl Ether → HCID 12985406, compound

HRID 431448Notes

Reaction equation

HRID 431448 reaction equation
[OH:1][CH:2]([CH2:14][Br:15])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[O:16]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)C>ClCCl>[O:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[O:1][CH:2]([CH2:14][Br:15])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 12985405HCID 12985405, compound

Product 1

HCID 12985406HCID 12985406, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzal 3-[2-tetrahydropyranyloxy]-4-Bromobutanoate. The product of step 2 (845 mg, 3.09 mmoles) was dissolved in dichloromethane (10 mL), and dihydropyran (300 μL, 277 mg, 3.29 mmole) and p-toluenesulfonic acid monohydrate (3 crystals) were added. The solution was stirred at room temperature for 1.5 h. Diethyl ether (40 mL) was then added, and the solution was washed with saturated sodium bicarbonate (2×40 mL), dried over anhydrous sodium sulfate, and evaporated. Purification by column chromatography using ethyl acetate-hexanes (3:7) gave benzyl 3-[2-tetrahydropyranyloxy]4-bromobutanoate (1.07 g, 97%) as a 1:1 mixture of diastereoisomer. IR (neat): 3033, 1737 cm−1. Mass spectrum (CI, m/z): 357, 3539 (M+1, m+3). Calcd. for C16H21BrO4: C 53.75; H 5.88. Found: C 53.65; H 5.60.

Workup

  1. washthe solution was washed with saturated sodium bicarbonate (2×40 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-33b74fc57caf42ce924146ae4f77e6ef
Source dataset
uspto-grants-2003_12
Patent number
US06660734B1

Reaction notes

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