3-Mercaptopropionic Acid → HCID 54324610, compound

HRID 1981219Notes

Reaction equation

HRID 1981219 reaction equation
C(C(C)[C:11]([OH:13])=S)C=CC1C=CC=CC=1.C(Br)C=CC1C=CC=CC=1.C(C(O)=O)CS.[CH2:31]([S:40]([CH:43]([CH3:47])C(O)=O)(=[O:42])=[O:41])[CH:32]=[CH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.C(OCC)(=O)C>[OH:13][CH2:11][CH2:47][CH2:43][S:40]([CH2:31][CH:32]=[CH:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)(=[O:41])=[O:42]

Participants

8

Reactant 5

HCID 65143-Mercaptopropionic AcidHCID 98116BromomethylstyreneHCID 21226445Aluminium lithium hydrideHCID 70486868HCID 70486868, compoundHCID 178442107HCID 178442107, compound

Product 1

HCID 54324610HCID 54324610, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cinnamylthiopropionic acid, m.p. 87° C., was prepared from cinnamyl bromide and mercaptopropionic acid and oxidised by the method described in Example 23(a) to cinnamylsulphonylpropionic acid, m.p. 160° C. This acid was reduced by addition to a stirred suspension of lithium aluminium hydride (2 equivalents) in tetrahydrofuran at -20° to -25° C. and the product formed isolated by ethyl acetate extraction to give cinnamyl 3-hydroxypropyl sulphone, m.p. 86° C. A solution of cinnamyl 3-hydroxylpropyl sulphone, para-toluene sulphonic acid (catalytic) and dihydropyran (2 equivalents) in dichloromethane was allowed to stand at room temperature for 24 hours, evaporated, and recrystallised from diethyl ether to give the title compound, m.p. about 45° C.

Workup

  1. customthe product formed

Sources & evidence

ORD record
ord-d2f28d0d92394e31937038c994426e3e
Source dataset
uspto-grants-1985_04
Patent number
US04513005

Reaction notes

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