Tetrahydrofuran → (S)-1-phenylmethoxy-4-penten-2-ol

HRID 54761Notes

Reaction equation

HRID 54761 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1C[CH2:15][CH2:14][CH2:13]1>>[C:2]1([CH2:1][O:8][CH2:9][C@@H:10]([OH:11])[CH2:15][CH:14]=[CH2:13])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 108989(Phenylmethoxy)acetaldehyde

Product 1

HCID 11830274(S)-1-phenylmethoxy-4-penten-2-ol

Procedure

The optically active tetrahydrofuran derivatives are prepared according to Scheme V. Benzyloxyacetaldehyde is reacted with optically active 2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylic acid ester, XVII, to give optically pure (S)-1-phenylmethoxy-4-penten-2-ol, XVIII. Cyclization of alcohol, XVIII, with iodine in the presence of sodium bicarbonate gives a mixture of optically pure 2,5-anhydro-1,3-dideoxy-1-iodo-D-threopentitol, XIX, ##STR112## and 2,5-anhydro-1,3-dideoxy-1-iodo-D-erythro-pentitol, XX, which is separated by flash chromatography using silica gel. ##STR113##

Sources & evidence

ORD record
ord-05c0d30e7a1e4092a5effc54b2762f22
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

Loading…