Diethyl Ether → HCID 12985406, compound

HRID 2184665Notes

Reaction equation

HRID 2184665 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

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 diastereisomers. 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-1a1d34bff0374cff8589f0821bda5945
Source dataset
uspto-grants-2002_06
Patent number
US06399600B1

Reaction notes

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