Hydrogen Peroxide → HCID 70478770, compound
Reaction equation
[O:1]1C=CCCC1OOC.[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH:11]1[CH2:16][OH:17].[CH3:18][CH2:19][O:20][CH2:21][CH3:22].B.OO.[OH-].[Na+]>O1CCCC1>[OH:1][CH:14]1[CH2:15][O:10][CH:11]([CH2:16][OH:17])[CH2:12][CH2:13]1.[CH3:18][CH2:19][O:20][CH2:21][CH3:22]Participants
Procedure
A dihydro-2H-pyran-2-ylmethoxy ether of Formula 1 is an especially useful intermediate to the ethers of formula 1 in which R is, e.g. hydroxy, oxo, methylene, alkyl or alkoxy by use of conventional synthesis techniques. For example, (3,4-dihydro-2H-pyran-2-yl)methanol ether is treated with, e.g. borane in tetrahydrofuran followed by hydrogen peroxide and sodium hydroxide, to give the corresponding (3,4,5,6-tetrahydro-5-hydroxy-2H-pyran-2-yl)methanol ether. This hydroxy ether is treated with, e.g. oxalyl chloride in dimethyl sulfoxide, to obtain the corresponding (3,4,5,6-tetrahydro-2H-5-oxo-pyran-2-yl)methanol ether. This oxo ether is treated with, e.g. methyl triphenyl phosphonium bromide, to obtain the corresponding (3,4,5,6-tetrahydro-2H-5-methylene-pyran-2-yl)methanol ether. This ether is treated with, e.g. hydrogen in the presence of platinum oxide and ethyl acetate, to give the corresponding (3,4,5,6-tetrahydro-2H-5-methoxypyran-2-yl)methanol ether.
Sources & evidence
- ORD record
- ord-c910178501eb42cc91fa3e4f665ab612
- Source dataset
- uspto-grants-1985_06
- Patent number
- US04525203
Reaction notes
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