Methyl 4-iodobenzoate → Methyl 4-[3-hydroxy-3-(4,4-dimethylthiochroman-6-yl)-1-propynyl]benzoate

HRID 840484Notes

Reaction equation

HRID 840484 reaction equation
[C:1]([CH:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[S:11][CH2:10][CH2:9][C:8]2([CH3:16])[CH3:15])[OH:4])#[CH:2].I[C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1>>[OH:4][CH:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[S:11][CH2:10][CH2:9][C:8]2([CH3:16])[CH3:15])[C:1]#[C:2][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 69273Methyl 4-iodobenzoateHCID 22619414alpha-Ethynyl-4,4-dimethyl-6-thiochromanmethanol

Product 1

HCID 22619407Methyl 4-[3-hydroxy-3-(4,4-dimethylthiochroman-6-yl)-1-propynyl]benzoateYield 68.2%

Procedure

Following the basic procedure of Example 11(d), by reacting 1.4 g (6 mmol) of α-ethynyl-4,4-dimethyl-6-thiochromanmethanol with 1.6 g (6 mmol) of methyl 4-iodobenzoate, 1.5 g (68%) of the expected ester was obtained in the form of an orange-colored oil.

Sources & evidence

ORD record
ord-2747924c3b134eb69feb96f896e8dc78
Source dataset
uspto-grants-2002_04
Patent number
US06368608B1

Reaction notes

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